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

Nathan Osborn | Montgomery Little & Soran, PC

Nate Osborn is an equity shareholder with Montgomery Little & Soran, PC, in Greenwood Village, Colorado. His practice is focused on real estate litigation and real estate transactions. In addition to his work for clients, Mr. Osborn can be hired as an expert witness in cases involving real estate issues. Mr. Osborn is a trial attorney and has tried 62 cases in his career. He received the highest “AV Preeminent” rating from Martindale Hubbell in 2014 and has maintained this rating since then. He was recognized as a “Super Lawyer” in 2025. Mr. Osborn is licensed to practice in Colorado and Nebraska.

Joffrey Long | Southwest Bancorp

Joffrey Long is the President of Southwest Bancorp, a private money investor/lender that makes, arranges, and services private money loans.

He is the Past President of the California Mortgage Association (CMA) and has also served as its Education Chair. He’s currently a member of the CMA Education Committee and a member of its Board of Directors.

He has previously served as an expert witness in matters relating to private money lending and loan servicing and has testified in related depositions, arbitrations and trials.

Kevin Jerry | Kevin A. Jerry, MST & Associates

Kevin Jerry is a nationally recognized expert in Tax Method Changes. He specializes in Cost Segregation, Tangible Property Regulations, and revenue recognition changes. Kevin graduated with honors from the University of Cincinnati with a Master of Science Degree in Real Estate Taxation. Over the last ten years, he has worked with some of the largest property owners in the country. He is also a sought-after speaker on the Tangible Property Regulations, the Real Estate Professional certification, and the nuances and complexities of Cost Segregation. Kevin has spoken at such venues as the American Institute of Certified Public Accountants, the Kentucky CPA Association, the Florida CPA Association, the Hong Kong Trade Association, and the California CPA Association.

Robert H.D. Genders | Investment Counsel Exchange

Our speaker, Robert H.D. Genders, Esq., is an accomplished 1031 executive and corporate attorney with over 25 years of extensive experience advising in real estate, specializing in Investment Exchanges, Corporate Law, & Title Insurance. As a Principal of Investment Counsel Exchange (ICE), he brings a wealth of knowledge and leadership to the firm, drawing on his diverse background across multiple facets of the real estate and legal sectors.

Throughout his career, Robert has emphasized collaboration, working closely with and training financial advisors, attorneys, brokers, title agencies, CPA’s, and other professionals to drive successful outcomes for their business. Holding positions as corporate counsel, exchange counsel, and owning a regional title agency furthered his deep understanding of tax-deferred investment strategies like IRC Section 1031/1033 & DST exchanges, combined with his ability to foster industry relationships, positions him as a trusted leader providing expert counsel and innovative solutions. By focusing on team-driven success, ICE consistently delivers value to both clients and partners. [email protected]

Dov Treiman | Adam Leitman Bailey, P.C.

Mr. Treiman has been a partner at Adam Leitman Bailey P.C. since 2006 and chairs the Landlord-Tenant Civil Litigation Practice.

Mr. Treiman was involved in private practice for fifteen years before devoting his principal time to the collecting, editing, writing, and publishing of scholarly research materials in landlord-tenant law. His writings include numerous articles in the New York Law Journal and many articles in the Landlord-Tenant Practice Reporter.

Mr. Treiman was the Founding Editor and Contributor of a great many articles to Landlord Tenant Monthly (4 volumes); Editor and Commentator, The Housing Court Reporter (24 volumes); Editor and Commentator, Treiman’s Commentaries (3 volumes); Editor, The Housing Court Reporter Chronological Annotator (3 volumes); Editor, The Housing Court Reporter Plaintiff-Defendant Tables (2 volumes); Editor, The Housing Court Reporter Digest (7 volumes); Editor and Commentator, Treiman’s New York Landlord Tenant Statutes Annotated (3 volumes); Editor and Commentator, Treiman’s Rent Stabilization Code Annotated (3 volumes); Editor and Author, Treiman’s Trial Manual; Editor and Principal Author, Treiman’s Encyclopedia and Dictionary (2 volumes); Editor and Commentator, Treiman’s Leading Cases (2 volumes); Editor, Public Documents of the DHCR; Editor, The Loft Board Reporter (18 volumes); Editor, The New York City Administrative Law Reporter (3 volumes); Editor, Landlord Tenant Appellate Reporter (7 volumes).

Of these, undoubtedly, the most important is the Housing Court Reporter, the standard work used by all the New York City courts and all quality practitioners of landlord-tenant law to search through some 50,000 cases for applicable precedents for appellate briefs, legal documents and motions.

Mr. Treiman was also commissioned by the State of New York to produce special editions of several of these works for their use in chambers by each of the Housing Judges.

In all, Mr. Treiman has written over 80 volumes on the subject of landlord-tenant law and has often been quoted as authority in decisions written by the various courts and by other legal commentators. 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 has created customized versions of many of these documents for the firm’s clients. Mr. Treiman has also written several other books on non-legal topics, both fiction and non-fiction.

Mr. Treiman is a highly sought lecturer on landlord-tenant subjects and has been retained by most of the providers of Continuing Legal Education in New York State. He was the principal consultant to the New York Times for landlord-tenant matters. Mr. Treiman is the Chair of the Board of Advisors of the Apartment Law Insider.

Mr. Treiman has been recognized for this work with featured biographies in Who’s Who in American Business, Who’s Who in American Law, Who’s Who in America and has been designated in AVVO as “Superb,” and has repeatedly been designated as a Super Lawyer. Mr. Treiman earned his Bachelor’s Degree from the State University of New York at Stony Brook and his Juris Doctor from St. John’s University, School of Law. Mr. Treiman has also received certificates from the Hebrew University in Jerusalem and from Princeton Theological Seminary “With Distinction.” Mr. Treiman has studied numerous languages and is strongly conversant in several of them.

Session I – Real Estate LLC Structuring | 1:00pm – 2:00pm

• Determining entity structure
• Advantages of LLCs
• What is the potential liability?
• Operating agreement drafting tips
• 1031 exchanges

Break | 2:00pm – 2:10pm

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

• When to segregate
• How to expense trash during renovation
• How to expense removal costs
• How to expense many major repairs that CPAS depreciate

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

• Timing discipline & common pitfalls
  • Navigate the 45-day identification and 180-day closing deadlines, avoid mismatches, and prevent costly missteps like boot
• Reverse & improvement exchanges
  • Acquire replacement property first (reverse) or use exchange funds for construction or enhancements (improvement), all within strict timelines
• Partnership & complex ownership structures
  • Handle exchanges involving partnerships, LLCs, TICs, or DSTs effectively while avoiding taxable pitfalls like “boot”
• Partial & multiple-property exchanges
  • Defer taxes while accessing liquidity or diversifying by exchanging into several properties with strategic planning

Break | 3:10pm – 3:20pm

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

• How lenders view LLC as a property owner and/or as a borrower
•  Workarounds for financing when title is now in the LLC
• Challenges with existing lenders when transferring property to an LLC
• How property insurance carriers view LLCs as their new “insured,” and what to do about it
• Preparing clients for lending and insurance challenges both before and after acquisition or transfer of property into an LLC

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

• The reasons tenants want to have these short term stays and landlords and municipalities want to prevent them
• Vulnerabilities to owners of LLCs from ordinances passed to control short term rentals
• Vulnerabilities to owners of LLCs from general purpose ordinances that have unexpected application to short-term rentals
• Vulnerabilities to owners of LLC’s from employing self-help