Raising equity deal-by-deal slows sponsors down and drains resources. By leveraging Delaware Statutory Trusts (DSTs) and 721 UPREIT exchanges, operators can unlock liquidity, attract motivated 1031 investors, and gain long-term alignment with institutional capital—without selling control or restarting fundraising every deal. DSTs provide passive investor demand, tax-deferred recapitalization, and simplified ownership, while 721 UPREITs offer portfolio diversification, tax deferral, and future liquidity via REIT shares. Combined, these strategies create a powerful cycle that frees sponsors from the fundraising treadmill and builds scalable, enduring growth with institutional alignment.

Selling appreciated property often triggers capital gains taxes and depreciation recapture, wiping out hundreds of thousands in potential reinvestment capital. A Delaware Statutory Trust (DST), used in a 1031 exchange, allows owners to defer both taxes while reinvesting 100% of their equity into professionally managed, income-producing real estate. DSTs also provide passive income, diversification, and estate-planning advantages—with options like a 721 UPREIT conversion for future liquidity and succession clarity. With Medalist’s focus on secure, single-tenant net lease properties, investors gain stability, tax efficiency, and long-term legacy protection.

For property owners age 60+, managing rentals often becomes more burden than benefit. Delaware Statutory Trusts (DSTs) provide a smarter alternative—delivering steady, passive income, full 1031 tax deferral, diversification, and simplified estate planning without the headaches of tenants or property upkeep. By exchanging into DSTs, owners can preserve equity, secure predictable distributions from institutional-grade assets, and pass along a clear legacy to heirs. With Medalist’s focus on single-tenant net lease properties, investors gain stability and peace of mind—freeing them to enjoy retirement while their wealth continues working.

Delaware Statutory Trusts (DSTs) let charitable, real-estate-rich donors turn appreciated property into tax-smart impact and passive income. By splitting proceeds into a debt-free DST for charity (generating income and an immediate charitable deduction) and a leveraged DST for the family (deferring capital gains and depreciation recapture while paying passive income), donors can support ministries, preserve wealth, and simplify estates—all within IRS-compliant structures. Medalist handles sale, structuring, and delivery of assets (e.g., REIT shares for charities), creating a clean, flexible path to give now, keep income, and plan a lasting legacy.

For many longtime property owners, downsizing isn’t just about a smaller home—it’s about unlocking equity, reducing costs, and simplifying life while preserving wealth for the next generation. Whether driven by high property taxes, overwhelming upkeep, health or mobility needs, or the desire to be closer to family, downsizing can open the door to passive income solutions like DSTs and NAV REITs. With Medalist’s guidance, owners can make this transition tax-efficient, stress-free, and legacy-focused—turning real estate into a platform for financial freedom and long-term security.

Every portfolio has its crown jewels—high-performing assets that deliver income, appreciation, and stability. Selling them often leads to lost cash flow, heavy tax bills, and reinvestment risk. Instead, strategies like 721 UPREIT contributions, 1031 exchanges, and DSTs allow owners to unlock liquidity, defer taxes, diversify, and maintain steady income—without giving up their best properties. With thoughtful planning, investors can retain long-term winners while still accessing growth capital and estate advantages.

For retiring landlords, Delaware Statutory Trusts (DSTs) offer the perfect way to transition from hands-on property management to hands-free, passive income. By deferring capital gains taxes through a 1031 exchange, landlords can preserve equity, diversify into institutional-grade properties, and enjoy professional management without tenant headaches. DSTs also simplify estate planning by providing fractional ownership interests that are easy to transfer, while optional 721 UPREIT conversions add future liquidity and flexibility. For many property owners, DSTs deliver both financial security and a lifestyle upgrade—making retirement simpler, safer, and more enjoyable.

Selling top-performing properties often means losing compounding returns, steady income, and tax efficiency. A smarter alternative is contributing assets to a REIT’s Operating Partnership in exchange for OP Units. This structure lets investors defer capital gains taxes, retain income through quarterly distributions, diversify instantly, and simplify estate planning—all while avoiding the risks of selling and replacing assets. Permanent capital platforms give owners liquidity and stability, ensuring their wealth keeps working without sacrificing long-term upside.

Family portfolio transitions can strain even the most successful families—conflicting risk appetites, unclear leadership, and uneven benefit distribution often create discord. Effective family governance solves these challenges by establishing a clear investment mandate, decision-making framework, estate planning integration, and knowledge transfer systems. Regular family meetings, third-party advisors, and financial literacy initiatives ensure smoother generational handoffs and preserve institutional memory. With strong governance in place, families can safeguard wealth, reduce conflict, and align values across generations—turning transitions into opportunities for both stability and legacy.

In a world of inflation, high interest rates, and volatile markets, Triple Net Lease (NNN) properties shine as a safe haven for investors in 2025. With tenants covering taxes, insurance, and maintenance, NNNs deliver predictable, inflation-hedged income backed by long-term leases and creditworthy, essential-business tenants. Add in powerful tax advantages—from 1031 exchanges to UPREIT conversions—and these assets offer not just stability, but also estate planning and diversification benefits. For sponsors, family offices, and retirees alike, NNN properties provide the rare combination of steady income, resilience, and tax efficiency in uncertain times.

Portfolio transitions can disrupt income through timing mismatches, temporary gaps, and rising costs. To keep cash flow steady, investors should adopt both tactical measures—like staggering transactions, using bridge capital, prioritizing income-driven assets, locking lease continuity, and maintaining reserve funds—and strategic frameworks like the permanent capital model, which smooths income through diversification and predictable distributions. By planning ahead, families and sponsors can transform portfolio transitions from stressful disruptions into opportunities for growth, stability, and long-term wealth preservation.

When deciding whether to convert properties into REIT shares or retain them directly, investors should weigh tax deferral, passive income, and liquidity benefits against personal flexibility and strategic goals. Assets with creditworthy tenants, long-term leases, and significant appreciation are strong REIT candidates, offering stability and tax-efficient compounding. In contrast, value-add projects, strategically important locations, or properties needed for personal flexibility may be better held directly. The key is aligning each asset’s role with your broader portfolio objectives, ensuring diversification, tax efficiency, and long-term wealth preservation.