The Ultimate Guide to Advising on Short-Term Rentals: Zoning Conflicts, Tenant Protections, LLC Formation, Tax Exposure, and Regulatory Defense

Dov Treiman
Solomon Chouicha
Carolyn Z. Rualo
Gregory M. Taube
Glenn D. Wright
Dov Treiman | Adam Leitman Bailey
Solomon Chouicha | Adam Leitman Bailey
Carolyn Z. Rualo | Adam Leitman Bailey
Gregory M. Taube | Nelson Mullins Riley & Scarborough
Glenn D. Wright | Wright Law Firm

Live Video-Broadcast: August 15, 2025

3 hour CLE

Tuition: $245.00
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Program Summary

Session I - Legal Risks in Short-Term Rentals: Liability, HOA Compliance, and Lease Enforcement – Greg Taube

The rapid growth of short-term rentals through platforms like Airbnb and Vrbo has introduced a complex web of legal challenges for property owners, landlords, and community stakeholders. Attorneys advising clients in real estate, landlord-tenant law, or property management must now grapple with emerging issues ranging from municipal zoning disputes and HOA restrictions to guest liability and enforceability of short-term lease agreements. This session will provide a comprehensive legal review of the key risks and evolving jurisprudence surrounding short-term rental properties. Drawing from his litigation background and experience presenting related topics, Greg Taube will explore practical strategies for drafting enforceable guest agreements, managing lease disputes, and addressing compliance failures with HOAs and municipalities.

Key topics to be discussed:

  • Enforceability of short-term rental lease and guest agreements
  • Homeowners’ Association (HOA) and condominium rules: Legal tensions and enforcement trends
  • Municipal regulation and zoning compliance
  • Liability and risk exposure for owners and managers

Session II - LLCs, Tax Benefits, and Operational Hurdles: Legal Strategies for Short-Term Rental Hosts – Glenn D. Wright

Short-term rentals are rapidly gaining popularity, but they also present a range of legal, tax, and operational challenges. This session offers a comprehensive legal guide for property owners and attorneys working with platforms like Airbnb and VRBO. We’ll explore the pros and cons of forming an LLC, including how it can provide liability protection and enhance credibility with lenders and vendors. Attendees will also gain insight into key tax considerations, such as eligibility for the Qualified Business Income (QBI) deduction, pass-through taxation benefits, and how the IRS distinguishes between material and passive participation. Beyond legal structure and taxation, the session will address operational complexities, including managing platform relationships, complying with evolving local regulations, and developing hospitality-focused protocols for guest services, maintenance, and emergencies.

Key topics to be discussed:

  • Advantages and disadvantages of forming an LLC for short-term rentals on platforms like Airbnb and VRBO
  • Tax advantages
  • Operational challenges

Session III - Rent Stabilization, Tenant Protections, and Regulatory Conflict in Short-Term Rentals – Dov Treiman, Solomon Chouicha, and Carolyn Z. Rualo

As cities increasingly crack down on short-term rentals, landlords face complex conflicts between local STR regulations and tenant protection laws such as rent stabilization and harassment prevention statutes. This session will examine how short-term rental use collides with longstanding landlord-tenant frameworks, especially in jurisdictions like New York. Attendees will gain critical insights into lease structuring, enforcement strategies, and how to defend or challenge claims involving STR misuse, illegal sublets, or violations of housing codes and stabilization laws.

Key topics to be discussed:

  • Short-term rentals & rent stabilization: When tenants use Airbnb, what’s allowed, what’s illegal
  • Harassment claims: How STR practices can trigger unlawful eviction or harassment claims
  • Enforcement from a landlord perspective: Drafting leases to prevent unauthorized STRs
  • Regulatory collisions: Navigating overlapping STR rules, tenant protections, and city enforcement
  • Housing court trends: Recent rulings and case law involving STR misuse and stabilization conflicts

This course is co-sponsored with myLawCLE.

Date / Time: August 15, 2025

  • 1:00 pm – 4:20 pm Eastern
  • 12:00 pm – 3:20 pm Central
  • 11:00 am – 2:20 pm Mountain
  • 10:00 am – 1:20 pm Pacific

Closed-captioning available

Speakers

Dov Treiman_myLawCLEDov Treiman | Adam Leitman Bailey

Mr. Treiman has been a partner at Adam Leitman Bailey P.C. since 2006 and co-manages the Landlord-Tenant Civil Litigation Practice. As one of the leading authorities in the landlord-tenant bar, Mr. Treiman’s drafting of appellate briefs, legal documents and motions has increased the ability of the firm to garner better results for its clients.

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 51 Housing Judges. He has been retained by Lexis-Nexus to produce their Practical Advice on Residential Landlord Tenant Proceedings in New York.

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 fourteen languages and is strongly conversant in several of them. He and his husband, firm administrator Tom Treiman, work together on numerous projects for the firm.

 

Solomon Chouicha | Adam Leitman Bailey

Solomon is a real estate attorney practicing landlord-tenant litigation and State Supreme Supreme Court Litigation. Most recently he was an associate at Gutman Mintz Baker & Sonnenfeldt, LLP, a boutique law firm in Long Island specializing in landlord-tenant matters. Previously he worked for District Council 37’s Municipal Employees Legal Services, where he represented union members and retirees in Housing Court, and for Legal Services of the Hudson Valley, where he represented indigent clients in Dutchess County on a variety of matters including landlord-tenant, Social Security Disability appeals, and Veterans’ disability cases. Solomon received his BBA from Baruch College, and then worked for two years as a paralegal at the Brooklyn District Attorney’s Office. He attended law school at the University of Iowa and resides in Brooklyn.

 

Carolyn Z. Rualo | Adam Leitman Bailey

Carolyn Z. Rualo is a Partner in the firm’s Landlord-Tenant and Rent Regulatory Due Diligence and Transactional Risk Assessment of Multi-Family Dwellings Groups and has been with Adam Leitman Bailey, P.C. since 2007. She represents a wide spectrum of New York City landowners from beginning property investors of small to mid-size multiple dwellings to seasoned property owners of hundreds of residential buildings throughout the City of New York. Her expertise in helping both her property owner clients and tenant clients in understanding the complex rent regulations and laws that govern their buildings allows her to see not only her strongest case, but her adversaries’ anticipated positions. She can thus frame a response even before the other side has thought what to answer.

She represents both commercial and residential landlords and tenants before the state courts of New York, the New York City Civil Courts, Homes and Community Renewal of the State of New York (HCR), formerly the Division of Housing and Community Renewal of the State of New York, and the Certificate of No Harassment Unit of the Department of Housing Preservation and Development (HPD) of the City of New York. She specializes in investigating and uncovering rent regulatory non-compliance issues that can subject current and potential building owners to hundreds of thousands of dollars in future liability for rent overcharge exposure and building wide permanent rent reductions. Similarly, she successfully secures the return of overpaid rent and buyouts for her tenant clients. Buyers of multiple dwellings have relied on her and her team to review up to hundreds of units in multi-property portfolios, within narrow due diligence periods, and advise on issues that warrant special negotiations to ensure the value of their investment. Carolyn Rualo is particularly sensitive to the tight time frames these investigations require. With over ten years experience of practice before the Housing Courts of the City of New York and the Supreme Court of the State of New York, she also prosecutes and defends clients in nonpayment proceedings, holdover proceedings, Housing Part (HP) proceedings and in cases to determine an apartment’s rent regulatory status, legal regulated rent and any rent overcharge liability, for individual parties and in defending class action lawsuits against building owners.

Carolyn Rualo’s clients authorize her to process applications and defend actions before the HCR, including applications for rent increases based on Major Capital Improvements (MCIs), rent reduction applications, rent overcharge complaints, modification of services application, Tenant Protection Unit investigations and applications that seek an administrative determination by the agency as to an apartment’s legal rent or regulatory status. She also routinely educates and assists property owners in complying with their obligations to annually register their buildings with HCR and in correcting any registration errors that may have occurred in the past, often under prior ownership. Carolyn Rualo is relentless in making sure that her clients fully understand their positions’ strengths and weaknesses.

Carolyn Rualo is a leading attorney who has been recognized for her impressive accomplishments in real estate law. She has been named repeatedly as a Super Lawyers Rising Star and has also been featured as one of the Super Lawyers Top 50 Women Attorneys in the New York metropolitan area – one of only 18 real estate attorneys who made the list that year. Carolyn Rualo was recently named as one of New York Law Journal‘s “New York Trailblazers” for her innovative and unconventional approach in helping an owner avoid a City lien for three times the market cost for making emergency repairs. She was also recognized by the Chambers Women in Law Awards: USA 2018 as a nominee for the “Future Leader – Gender Diversity (Private Practice)” category, joining only four other women from across the nation.

Carolyn Rualo is admitted to practice law in New York and New Jersey. She is a graduate of Villanova University, College of Commerce & Finance, where she was a member of the Gamma Phi Honors Society. She then went on to earn her Juris Doctor from Brooklyn Law School before joining the firm in 2007. Carolyn Rualo is starting her 16th year at Adam Leitman Bailey, P.C.

 

Gregory M. Taube | Nelson Mullins Riley & Scarborough

Gregory M. Taube is a partner at Nelson Mullins in Atlanta, Georgia, where he brings over two decades of experience representing clients in complex commercial disputes involving real estate, finance, and contract law. His real estate litigation practice includes representing franchisors, landlords, and property owners in disputes stemming from purchase and sale agreements, leases, and franchise contracts. Greg also regularly advises clients on creditor rights, including matters involving mortgage lending, foreclosure defense, repossession, and distressed asset recovery. He has represented clients in state, federal, and bankruptcy courts across multiple jurisdictions, and is a trusted advisor for creditors, lenders, and property stakeholders navigating real property challenges.

Greg’s real estate and financial litigation insights have been featured in CLE programs and industry seminars, including presentations on title insurance, foreclosure procedures, and real estate development law. He is a recognized authority in bankruptcy and creditors’ rights, named in The Best Lawyers in America® for Bankruptcy and Insolvency Law (2020–2025), and has served in leadership roles with the American and Atlanta Bar Associations. Greg holds a J.D., summa cum laude, from the University of Alabama School of Law and is admitted to practice in both Georgia and Alabama.

 

Glenn D. Wright | Wright Law Firm

Glenn D. Wright leads the Wright Law Firm’s commercial real estate and litigation practice in New York City, bringing extensive experience in leasing and real estate dispute resolution. He advises clients across the NYC metropolitan area on retail and office lease negotiations, lease assignments, subleases, “good guy” guarantees, and strategic early terminations. Glenn also regularly represents landlords and tenants in complex commercial lease and real property litigation, handling matters ranging from holdover proceedings and title disputes to easement conflicts, DOB violations, and eminent domain issues in both state and federal courts.

In recognition of his leadership in real estate law, Glenn was appointed to the New York City Bar Association’s Real Property Law Committee (Class of 2024), contributing to policy development and CLE programming on topics such as affordable housing and urban development. He is a prolific author and CLE speaker, with publications including “Key Considerations in Negotiating REBNY Office Leases” (Lexis‑Nexis, May 2025), “Billboard Leasing” (ABA Probate & Property Journal, May 2024), and “Evolution of the Pop‑Up” (May/June 2023). He also frequently presents nationally on commercial leasing issues like lease versus license arrangements, pop‑up leases, and billboard lease agreements.

Glenn is admitted to practice in New York State, and in the U.S. District Courts for the Southern, Eastern, and Western Districts of New York. He remains an active member of the NYC real estate legal community, including leadership roles with the NYC Bar and participation in national CLE programming and policy initiatives.

Agenda

Session I – Legal Risks in Short-Term Rentals: Liability, HOA Compliance, and Lease Enforcement | 1:00pm – 2:00pm

  • Enforceability of short-term rental lease and guest agreements
  • Homeowners’ Association (HOA) and condominium rules: Legal tensions and enforcement trends
  • Municipal regulation and zoning compliance
  • Liability and risk exposure for owners and managers

Break | 2:00pm – 2:10pm

Session II – LLCs, Tax Benefits, and Operational Hurdles: Legal Strategies for Short-Term Rental Hosts | 2:10pm – 3:10pm

  • Advantages and disadvantages of forming an LLC for short-term rentals on platforms like Airbnb and VRBO
  • Tax advantages
  • Operational challenges

Break | 3:10pm – 3:20pm

Session III – Rent Stabilization, Tenant Protections, and Regulatory Conflict in Short-Term Rentals | 3:20pm – 4:20pm

  • Short-term rentals & rent stabilization: When tenants use Airbnb, what’s allowed, what’s illegal
  • Harassment claims: How STR practices can trigger unlawful eviction or harassment claims
  • Enforcement from a landlord perspective: Drafting leases to prevent unauthorized STRs
  • Regulatory collisions: Navigating overlapping STR rules, tenant protections, and city enforcement
  • Housing court trends: Recent rulings and case law involving STR misuse and stabilization conflicts

Credits

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