The Ultimate Guide to Forming LLC to Hold Rentals Properties: Structure, taxes, 1031s, mortgage financing, and short-term rental liabilities

Nathan G. Osborn, Equity Shareholder | Montgomery Little & Soran, PC

Nathan G. Osborn is an Equity Shareholder at Montgomery Little & Soran, PC, where he has built a distinguished practice at the intersection of real estate litigation, real estate transactions, and commercial litigation. Licensed to practice in both Colorado and Nebraska, Mr. Osborn brings a rare dual strength to his work: a seasoned trial attorney who has tried 65 cases, paired with the deep transactional expertise of a full-service corporate counsel. This combined perspective allows him to guide transactional clients around pitfalls that commonly lead to courtroom disputes, while bringing practical, transaction-informed insight to the cases he litigates. Beyond his client work, he is regularly retained as an expert witness in matters involving real estate issues, attorney fees, and trial-related questions.

• Education & Credentials

Mr. Osborn earned his Juris Doctor with Distinction in 2007, following a Bachelor of Arts from Texas Christian University in 2003. He is admitted to practice in both Colorado and Nebraska, giving him a cross-jurisdictional platform from which to serve clients throughout the Rocky Mountain and Great Plains regions.

• Recognition & Leadership

Mr. Osborn’s work has earned consistent recognition from the most respected evaluators in the legal profession. He received the AV Preeminent® rating from Martindale-Hubbell in 2014 — the highest possible rating for legal ability and ethical standards — and has maintained that distinction every year since. He was named a Super Lawyers Rising Star from 2018 through 2021 and has been recognized as a Colorado Super Lawyer in 2023, 2024, and 2025. He has also been honored as a Distinguished Faculty Member by the National Business Institute.

• Professional Involvement

A nationally sought-after speaker, Mr. Osborn has delivered well over one hundred continuing legal education programs for organizations including the National Business Institute, the Colorado Bar Association, myLawCLE, WealthCounsel, Halfmoon Education, and the Colorado Real Estate Symposium. His speaking portfolio spans the full breadth of real estate practice, from title insurance, easements, and boundary law to LLC formation, operating agreements, closings, land use, and legal ethics, as well as emerging topics such as the role of generative AI in real estate. He is a recurring presenter at the Colorado Bar Association’s Business, Tax, Probate, and Real Estate Luncheon, where he has delivered the annual Real Estate Case Law Update on multiple occasions. As a published author, his work has appeared in The Colorado Lawyer, Probate & Property Magazine (published by the American Bar Association), the Colorado Bar Association Real Estate Law Newsletter, and the Colorado Cattlemen’s Association Newsletter, with articles addressing topics such as the use of LLCs to purchase and own rental property, recent Colorado real estate case law, implied easements, and prescriptive easements. In his community, he volunteers as a youth basketball coach.

• Experience

Before joining Montgomery Little & Soran, Mr. Osborn served as a Deputy District Attorney in El Paso County, Colorado — foundational trial experience that continues to shape his courtroom approach today. Over the course of his career, he has tried 65 cases across a wide spectrum of real estate and commercial matters, including mineral interest disputes, title insurance contract litigation, lender fraud defense, homeowners’ association access disputes, fraudulent conveyance actions, construction defect litigation, judicial foreclosure, boundary and easement disputes, defamation defense, arbitrations involving business misappropriation, and defense of professionals against license complaints. His practice focuses on matters involving real estate title and access disputes, title insurance, boundary and partnership disputes, landlord-tenant matters and leases, foreclosures, title agent negligence, liens, easements, real estate purchases and sales, real estate development, operating agreements, real covenants, partitions, zoning compliance, private and inverse condemnation, treasurer’s deeds, vacation rental licensing, bad faith claims against title insurance companies, attorney fee disputes, defamation, and professional licensing defense. He serves a diverse client base that includes title insurance underwriters and agents; commercial and residential landlords and tenants; real estate agents, brokers, and brokerages; real estate developers; and medical professionals such as doctors, dentists and orthodontists, rehabilitation facilities, and physical therapy practices — for many of whom he acts as full-service corporate counsel.

Joffrey Long, President | Southwest Bancorp

Joffrey Long is a nationally recognized loan servicing expert witness and an active industry practitioner with more than four decades of experience in California real estate lending. As President of Southwest Bancorp — a loan servicer, maker, and arranger of both consumer-purpose and non-consumer-purpose real estate loans — Mr. Long brings something that sets him apart from many experts in the field: he is not a retired executive speaking from memory or a scholar commenting from the outside, but a working loan servicing professional whose opinions are grounded in day-to-day involvement with the industry as it operates today. He is frequently retained to testify in matters involving loan servicing, loan origination, and investment in real estate loans.

• Education & Credentials

Mr. Long is an approved instructor for the Nationwide Mortgage Licensing System (NMLS) continuing education program, a credential reserved for qualified industry professionals charged with training the next generation of licensed mortgage practitioners. His active status as a working loan servicer and President of Southwest Bancorp means that, unlike many experts whose knowledge predates the post-2007 regulatory landscape, his qualifications reflect direct, ongoing experience operating under today’s framework — including the Dodd-Frank Wall Street Reform and Consumer Protection Act and the California Homeowner Bill of Rights (HBOR).

• Recognition & Leadership

Mr. Long is a Past President of the California Mortgage Association, one of the most influential trade organizations serving the California mortgage lending industry, and he previously served as the Association’s Education Chair. His continued service on the CMA Board of Directors and Education Committee reflects the industry’s sustained recognition of his leadership, judgment, and educational contributions to the profession.

• Professional Involvement

Mr. Long is an active and sought-after voice in industry education. He participates extensively in seminar presentations addressing loan servicing, legal and regulatory compliance, mortgage lending, and private money lending, and he serves as a continuing education instructor for NMLS-approved coursework. Through his ongoing role on the California Mortgage Association’s Board of Directors and Education Committee, he helps shape the educational programming that informs mortgage professionals across the state on evolving standards, regulatory developments, and best practices. He testifies frequently across a broad range of mortgage-related disputes and is regularly retained by attorneys, parties, and triers of fact who benefit from his ability to clearly explain complex loan servicing concepts in accessible terms.

• Experience

Mr. Long has been active in California real estate lending since 1981, giving him more than 45 years of continuous industry experience spanning multiple economic cycles, the 2007 mortgage crisis, and the sweeping regulatory reforms that followed. As President of Southwest Bancorp, he oversees the servicing, making, and arranging of real estate loans for both consumer and non-consumer purposes, giving him direct operational familiarity with the full life cycle of a mortgage loan — from origination through servicing, payoff, and, where necessary, default administration and foreclosure. As a loan servicing expert witness, Mr. Long provides expert reports, declarations, consultation, deposition testimony, and trial testimony in matters involving loan servicing, loan origination, and investment in real estate loans. His expert work encompasses the full spectrum of issues that arise between borrowers and loan servicers — including Requests for Mortgage Assistance (RMAs), loan modification processing, forbearance agreements, alleged dual tracking and wrongful foreclosure, single point of contact (SPOC) requirements, Homeowner Bill of Rights and Dodd-Frank compliance, servicing transfers, impound and escrow account disputes, and payoff and reconveyance issues. He also advises disputes between investors and loan servicers, including matters involving fractionalized trust deeds and multi-lender loans under Section 10238 of the California Business and Professions Code, foreclosure trustee interaction, REO administration, investor reporting, and disbursement of investor funds.

Kevin A. Jerry, Owner and Founder | Kevin A. Jerry, MST & Associates

Kevin A. Jerry, MST, is a nationally recognized authority in real estate taxation and a leading voice in tax strategy for commercial and income property owners. As the owner and founder of Kevin A. Jerry MST & Associates (KAJMST), he has built the only firm in the United States dedicated exclusively to real estate tax strategies for commercial properties — a distinction that reflects both his depth of specialization and his commitment to serving an underserved segment of the tax advisory market. His expertise spans Tax Method Changes, Cost Segregation, Tangible Property Regulations (TPR), and Revenue Recognition Changes, and his firm holds the further distinction of being the only one in its industry approved to deliver continuing education courses to the CPA community. Mr. Jerry is also a Licensed Insurance Agent (National Producer Number 17788808), allowing him to offer an expanded suite of planning services to his clients.

• Education & Credentials

Mr. Jerry holds a Master of Science in Real Estate Taxation from the University of Cincinnati’s Carl H. Lindner College of Business, where he graduated with honors. This specialized graduate training — uncommon in the broader tax advisory field — provides the technical foundation for his practice and informs his nuanced command of the intersection between federal tax law and commercial real estate. He is also a Licensed Insurance Agent, NPN 17788808.

• Recognition & Leadership

Mr. Jerry’s standing in the profession is reflected in his firm’s unique credentials: KAJMST is the only firm in the United States focused exclusively on commercial real estate tax strategy, and the only firm in its industry authorized to provide continuing professional education to CPAs. Under his leadership, the firm has earned a reputation for innovation, integrity, and results — helping property owners reduce capital gains exposure, facilitate smoother 1031 exchanges, and unlock permanent deductions for building improvements and repairs. Clients and colleagues consistently recognize him for his dedication, strong relationships, and ability to deliver exceptional value through ethical, defensible tax reduction strategies.

• Professional Involvement

Mr. Jerry is a sought-after speaker whose thought leadership reaches professional audiences across the United States and internationally. His speaking engagements include presentations before the American Institute of Certified Public Accountants (on Tangible Property Regulations and Cost Segregation), the Kentucky CPA Association (Real Estate Professional Certification), the Florida CPA Association (Tax Method Changes), the California CPA Association (the complexities of Cost Segregation), and the Hong Kong Trade Association (Revenue Recognition Changes). Through these engagements — and through KAJMST’s approved continuing professional education programming — he equips CPAs and other practitioners with the technical knowledge needed to navigate mandatory Tangible Property Regulations under §263(a) and §481(a) adjustments, and to better serve their own commercial real estate clients.

• Experience

With more than fifteen years of specialized experience, Mr. Jerry has advised some of the largest commercial property owners in the United States, guiding them through complex federal tax landscapes to unlock meaningful financial benefits. Through KAJMST, he delivers a focused suite of services, including Cost Segregation Studies designed to accelerate depreciation deductions and improve cash flow; Tangible Property Regulations compliance under the mandatory 2013 framework governing asset improvements and repairs; Partial Asset Dispositions and Removal Cost Calculations to optimize tax outcomes during property sales and renovations; R&D Tax Credits; SIMERPs; and broader wealth-building strategies including affordable business valuations and tax-free retirement planning. The firm’s streamlined methodology enables projects to be completed in as little as two weeks, accompanied by regular progress updates and comprehensive audit defense services — including representation before the U.S. Tax Court when necessary. Mr. Jerry leads a dedicated team across offices in Castle Rock, Colorado; West Lafayette, Indiana; and Scottsdale, Arizona, with a practice philosophy rooted in integrity, innovation, and a commitment to empowering commercial property owners to achieve their financial goals through specialized, client-centered tax strategy.

Robert H.D. Genders, Principal | Genders Law & Legacy PLLC

Robert H.D. Genders, Esq., is the founder of Investment Counsel Exchange (ICE), a national, attorney-owned platform focused exclusively on the secure, compliant execution of §1031 exchanges. With more than 25 years of hands-on experience across real estate transactions, 1031 exchanges, title operations, corporate training, and investment-strategy consulting, Mr. Genders brings an unusually broad, real-world perspective to the complex landscape of tax-deferred investment. His professional footprint spans work as an in-house corporate attorney, national exchange attorney, CLE/CE educator, and title agency owner — a combination that enables him to advise clients not just on the legal architecture of a transaction, but on how it actually operates in practice. Through ICE, he focuses on education, strategy, and qualified intermediary support that help investors and professionals navigate 1031 exchanges, Delaware Statutory Trusts (DSTs), and multi-jurisdictional investment considerations with clarity and confidence.

• Education & Credentials

Mr. Genders has been licensed to practice law in Washington, D.C. since 2002. His legal practice is conducted exclusively through Genders Law & Legacy PLLC, a Washington, D.C.–licensed federal law firm, and is limited to federal matters. He is an approved continuing legal education and continuing education provider with the American Bar Association, the Federal Bar Association, the Florida Bar, and the Florida Department of Business and Professional Regulation (DBPR) — a multi-jurisdictional educator credential that reflects both the breadth of his subject-matter expertise and the trust placed in him by leading regulatory and professional bodies.

• Recognition & Leadership

As the founder of Investment Counsel Exchange, Mr. Genders leads a national qualified intermediary platform built around disciplined workflows, institutional safeguards, and experienced coordination for both straightforward and highly complex transactions across jurisdictions. He is widely recognized within the industry for his ability to train and collaborate with a diverse professional audience — including financial professionals, investors, attorneys, CPAs, title agencies, developers, and national underwriters — and for his forward-looking work integrating next-generation settlement technology, investor tools, and modernized exchange architecture into the 1031 process. His platform is also positioned at the forefront of digital-asset and tokenized real-estate workflow licensing, an emerging frontier in real estate investment.

• Professional Involvement

Mr. Genders is an active and sought-after educator and speaker on 1031 exchanges, DSTs, qualified intermediary best practices, fiduciary and settlement-process considerations, and multi-jurisdictional investment strategy. His approved status as a CLE/CE provider with the American Bar Association, the Federal Bar Association, the Florida Bar, and the Florida DBPR gives him a national platform for delivering substantive training to attorneys, CPAs, title professionals, and financial advisors. He maintains and curates a vetted professional network — spanning certified tax advisors, financial wealth advisors, real estate brokers and agents, and jurisdiction-specific attorneys — enabling clients to connect with the right specialists for needs that fall outside ICE’s educational and qualified intermediary services. Speaking engagements and educational inquiries are welcomed through Investment Counsel Exchange.

• Experience

Over the course of a 25-plus-year career, Mr. Genders has built experience across national 1031 exchange platforms, multi-state real estate operations, digital-asset workflow development, and the design of investor-focused educational programs. His prior roles as an in-house corporate attorney, national exchange attorney, and title agency owner give him unusual fluency in both the legal and operational dimensions of real estate and tax-deferred transactions — from the drafting table to the closing table, and from day-to-day title workflow to cross-jurisdictional exchange coordination. Today, through Investment Counsel Exchange, he leads a practice focused on complex 1031 exchange workflows and qualified intermediary services, Delaware Statutory Trust (DST) education and coordination, multi-jurisdictional investment considerations, fiduciary and settlement-process insights, digital-asset and tokenized real estate workflow licensing, and qualified intermediary best practices and compliance awareness. Through Genders Law & Legacy PLLC, he separately provides federal legal services from Washington, D.C. Together, these complementary roles allow Mr. Genders to serve as both a trusted educator to the profession and a strategic guide to investors seeking to navigate the modern 1031 landscape with institutional-grade rigor.

Dov A. Treiman, Partner | Adam Leitman Bailey, P.C.

Dov A. Treiman is a Partner at Adam Leitman Bailey, P.C., where he co-manages the firm’s Landlord-Tenant Civil Litigation Practice and stands among the most respected authorities in the New York landlord-tenant bar. A partner at the firm since 2006, Mr. Treiman brings a rare combination of strengths to his practice: the analytical rigor of a scholar who has written more than 80 volumes on landlord-tenant law, paired with the practical skill of a litigator whose drafting of appellate briefs, legal documents, and motions has meaningfully enhanced the firm’s ability to secure favorable outcomes for its clients. His scholarship is not merely academic — it is the reference material relied upon daily by the New York City courts and by leading practitioners throughout the state.

• Education & Credentials

Mr. Treiman earned his Juris Doctor from St. John’s University School of Law and his Bachelor’s Degree from the State University of New York at Stony Brook. He has also received certificates from the Hebrew University in Jerusalem and, “With Distinction,” from Princeton Theological Seminary. A lifelong student of language, Mr. Treiman has studied fourteen languages and is strongly conversant in several — a foundation that informs his precision in legal drafting and his unusual command of the interpretive nuance so often at the heart of landlord-tenant disputes.

• Recognition & Leadership

Mr. Treiman’s contributions to the profession have earned him some of the most enduring forms of recognition available to a practicing attorney. He has been featured in Who’s Who in American Business, Who’s Who in American Law, and Who’s Who in America; has been designated “Superb” by AVVO; and has been repeatedly recognized as a Super Lawyer. Perhaps the most telling measure of his standing, however, is that the State of New York commissioned him to produce special chambers editions of several of his works for use by each of the state’s 51 Housing Judges — a distinction that places his scholarship at the core of how New York’s housing courts function. He has also been retained by LexisNexis to author Practical Advice on Residential Landlord-Tenant Proceedings in New York, and his writings are regularly cited as authority in judicial decisions and by other legal commentators.

• Professional Involvement

Mr. Treiman is a highly sought-after lecturer on landlord-tenant law and has been retained by most of the major providers of Continuing Legal Education in New York State. He serves as Chair of the Board of Advisors of the Apartment Law Insider and previously served as the principal consultant to The New York Times on landlord-tenant matters. He is the Founding Editor of Landlord Tenant Monthly and a prolific contributor to publications including the New York Law Journal and the Landlord-Tenant Practice Reporter. His editorial portfolio includes The Housing Court Reporter (24 volumes), Treiman’s Commentaries (3 volumes), Treiman’s New York Landlord Tenant Statutes Annotated (3 volumes), Treiman’s Rent Stabilization Code Annotated (3 volumes), Treiman’s Trial Manual, Treiman’s Encyclopedia and Dictionary (2 volumes), Treiman’s Leading Cases (2 volumes), The Loft Board Reporter (18 volumes), The New York City Administrative Law Reporter (3 volumes), and Landlord Tenant Appellate Reporter (7 volumes), among others. Of these, The Housing Court Reporter stands as the standard reference — used by all New York City courts and by quality practitioners throughout the field to search more than 50,000 cases for applicable precedent.

• Experience

Before devoting his principal professional time to the scholarship that has come to define his career, Mr. Treiman spent fifteen years in private practice — foundational experience that continues to inform the practical, court-tested sensibility evident in his writing and litigation work. Since joining Adam Leitman Bailey, P.C. as a partner in 2006, he has built a practice that combines high-stakes landlord-tenant civil litigation with the authorship and ongoing maintenance of the reference works on which the New York bar depends. Mr. Treiman is a principal author of most of the standard form leases and related documents in use throughout the New York City area, and he has developed customized versions of many of these documents to meet the specific needs of the firm’s clients. In addition to his legal scholarship, he has authored several books on non-legal topics, both fiction and non-fiction — reflecting the breadth of intellectual curiosity he brings to every aspect of his work. He works closely alongside his husband, firm administrator Tom Treiman, on numerous firm projects.

SESSION 1 – Real Estate LLC Structuring | 1:00pm – 2:00pm

This session offers attorneys practical guidance on real estate LLC structuring, covering entity selection, asset protection, liability mitigation, operating agreement drafting, and leveraging LLCs in 1031 exchanges to optimize client investment and development outcomes.

BREAK | 2:00pm – 2:10pm

SESSION 2 – Three Critical Strategies that Must be Implemented to avoid Overpaying Taxes on Rental Real Estate | 2:10pm – 2:40pm

This session equips property owners with three IRS-approved tax strategies unknown to most CPAs, including when to segregate, expensing renovation trash and removal costs, and properly deducting major repairs typically depreciated, maximizing deferrals and deductions.

SESSION 3 – Real‑World Issues & Smart 1031 Solutions w/ Exchange Counsel | 2:40pm – 3:10pm

This CLE session explores advanced 1031 exchange strategies, including reverse, improvement, partnership, and multi-property exchanges. Attendees learn timing discipline, how to avoid boot, and navigate complex ownership structures to maximize tax deferral and portfolio growth.

BREAK | 3:10pm – 3:20pm

SESSION 4 – Financing and Insurance with the LLC as the “Owner” | 3:20pm – 3:50pm

This session examines how lenders and insurers view LLCs differently than individual borrowers, addressing financing workarounds, challenges with existing lenders during property transfers, insurance carrier concerns, and practical steps for entities holding real estate assets.

SESSION 5 – LLC Liability in the Age of Short-Term Rentals: Legal Risks and Municipal Enforcement | 3:50pm – 4:20pm