Structuring LLCs to Hold Rental Real Estate: Entity Formation, Asset Protection, Tax Strategy, and Litigation Risk (2026 Edition)

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

Nathan G. Osborn is an Equity Shareholder with Montgomery Little & Soran, PC, where his practice centers on real estate litigation, real estate transactions, and commercial litigation. He also serves as full-service corporate counsel to numerous real estate and medical businesses, and is frequently retained as an expert witness in matters involving real estate issues, attorney fees, and trial-related disputes. Licensed in Colorado and Nebraska, Mr. Osborn uniquely blends deep courtroom experience with sophisticated transactional knowledge to help clients avoid litigation, and to prevail when it cannot be avoided.

Education & Credentials

Mr. Osborn earned his Juris Doctor with Distinction in 2007 and holds a Bachelor of Arts from Texas Christian University (2003). He is admitted to practice in Colorado and Nebraska.

• Recognition & Leadership

Mr. Osborn has held the highest “AV Preeminent” rating from Martindale-Hubbell continuously since 2014. He was named a Super Lawyers – Rising Star from 2018 through 2021 and has been recognized as a Super Lawyer in 2023, 2024, and 2025. He is also a Distinguished Faculty Member of the National Business Institute.

• Professional Involvement

A nationally sought-after speaker and published author, Mr. Osborn has delivered dozens of continuing legal education presentations for organizations including myLawCLE, the National Business Institute, the Colorado Bar Association, WealthCounsel, Halfmoon Education, SproutEd, and Law Practice CLE. His topics span real estate LLC formation and disputes, operating agreements, title insurance, easements and boundaries, land use and zoning, real estate case law updates, trial advocacy, evidence, legal ethics, and generative AI in real estate. He is a regular presenter at the Colorado Bar Association’s Business, Tax, Probate, and Real Estate Luncheon and has presented at the Colorado Real Estate Symposium and the Colorado Defense Lawyers Association Trial Academy. His published works include “Using LLCs to Purchase and Own Rental Property” (Probate & Property Magazine, 2023), “In Case You Missed It: Recent Real Estate Case Law Highlights” (The Colorado Lawyer, 2021), “Implied Easements: The Complicated Cousin of the Express Easement” (The Colorado Lawyer, 2014), and “Prescriptive Easements in Colorado” (Colorado Bar Association Real Estate Law Newsletter, 2014). Mr. Osborn also volunteers as a youth basketball coach.

• Experience

Mr. Osborn is a seasoned trial attorney who has tried 65 cases, leveraging that courtroom experience to guide transactional clients away from litigation and to litigate effectively when disputes arise. His matters span real estate title and access disputes, title insurance, boundary disputes, partnership and landlord-tenant disputes, leases, foreclosures, title agent negligence, liens, easements, real estate purchases and sales, real estate development, operating agreements, real covenants, spurious liens, partitions, zoning compliance, private and inverse condemnations, treasurer’s deeds, vacation rental licensing, bad faith claims against title insurance companies, attorney fee disputes, defamation, and professional license defense. Representative trial work includes defending lenders against fraud and Ability-to-Repay claims, representing national title insurance underwriters in contract disputes, defending real estate brokers and other professionals in licensing matters, representing homeowners’ associations and condominium associations in access and construction defect disputes, representing real estate holding companies and LLCs in deed, lease, and conveyance actions, and representing property owners in mineral interest, easement, and boundary litigation. Before joining Montgomery Little & Soran, Mr. Osborn served as a Deputy District Attorney in El Paso County, Colorado.

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.

SESSION 1 – Entity Selection & Formation for Rental Properties: Getting the Structure Right at the Start | 1:00pm – 2:00pm

Explore when rental property should be held in an LLC, how client goals shape entity choice, and what formation mistakes create long-term exposure, covering single-member versus multi-member LLCs, Series LLCs, state selection, and financing alignment.

BREAK | 2:00pm – 2:10pm

SESSION 2 – The Fiduciary Bridge: Merging 1031 Exchange & LLC Velocity with Blockchain Integrity | 2:10pm – 3:10pm

Explore IRC §1031 foundations, history, and tax deferral; advanced delayed, reverse, and build-to-suit exchange structures; the 45-day and 180-day rules; and a patent-pending verification framework ensuring legacy assets remain legal, liquid, and optimized.