Why Medalist’s Permanent Capital Platform Outperforms Deal-by-Deal Models
For decades, real estate owners, family offices, and investors have relied on a deal-by-deal approach, buy a property, manage it, eventually sell it, pay taxes, and start again. While familiar, this cycle often creates stress, inefficiency, and lost wealth. It forces investors to part with top-performing assets and exposes portfolios to unnecessary risk and tax drag.
Today, investors are demanding something better: a stable, tax-efficient, long-term platform where wealth can grow instead of being reset every time a property is sold. Medalist’s Permanent Capital platform delivers exactly that.
Below, we compare the challenges of the deal-by-deal model with the advantages of Permanent Capital, and show how Medalist’s DST-to-UPREIT structure empowers investors to protect wealth, grow income, and simplify their legacy.
The Persistent Struggles of Deal-by-Deal Fundraising and Ownership
Although traditionally used by sponsors, the same pitfalls of deal-by-deal thinking affect individual investors and families as well:
1. The Constant Scramble for Capital or Replacement Properties
Every sale creates a new problem:
Find another deal
Race through a 1031 exchange timeline
Underwrite assets under pressure
It’s stressful and time-consuming, and often leads to compromised decisions.
2. Selling Top-Performing Assets Too Soon
Investors frequently sell strong, income-generating properties simply to access cash or reduce management.
But selling a winner means losing:
Long-term appreciation
Ongoing passive income
A stable anchor inside the portfolio
It’s the opposite of compounding.
3. Erosion of Wealth Through Taxes
Deal-by-deal real estate ownership repeatedly triggers:
Capital gains taxes
Depreciation recapture
State taxes
This can eliminate 30–40% of equity every time a property trades hands.
4. Lack of Long-Term Strategy and Alignment
Deal-by-deal decision-making leads to:
Short-term thinking
Inefficient estate planning
Constant reinvention of the wheel
It’s transactional, not strategic.
These limitations are exactly why so many investors are now choosing a Permanent Capital structure, one that prioritizes income, deferral, stability, and legacy.
Medalist’s Permanent Capital Platform: A Smarter, Long-Term Solution
Medalist’s Permanent Capital platform replaces the old model with one built on alignment, tax efficiency, scalability, and compounding value.
It begins with a simple starting point: a Medalist DST.
1. Start With Stable Passive Income
Investors enter the Medalist ecosystem through a Delaware Statutory Trust, receiving:
Monthly passive income
Zero landlord responsibilities
1031 tax deferral
A debt-free or conservatively financed asset
Estate simplicity (easy transfer to heirs)
This creates the foundation for long-term wealth stability.
With a DST, investors are no longer forced to sell income-producing properties simply to lighten their workload. They can keep enjoying cash flow without the burden of active management.
2. Optional UPREIT Conversion for Long-Term Wealth
After the DST’s hold period (typically 2+ years), investors may choose, optionally, to complete a 721 UPREIT exchange, contributing their DST interest into the Medalist Operating Partnership.
This provides:
Full tax deferral
Conversion into a diversified, professionally managed portfolio
Access to Permanent Capital without triggering taxes
Potential liquidity options through REIT share structures
Long-term compounding power
This step is the bridge between passive income today and Permanent Capital growth tomorrow.
3. Long-Term Growth and Stability Through Permanent Capital
Once within the REIT, investors benefit from:
Liquidity & Flexibility
REIT shares create optionality that direct ownership simply cannot match.
Diversification
Instead of relying on one property or tenant, investors gain exposure across
markets, asset types, and credit profiles.
Sustainable Income
As a REIT, Medalist distributes at least 90% of taxable income, creating consistent, predictable yields.
Tax-Efficient Wealth Transfer
Heirs receive a simplified, income-producing asset rather than a complex property to manage or sell.
This is how Permanent Capital replaces transactional real estate with generational planning.
A Transferable, Scalable Model for Generational Success
Medalist’s Permanent Capital platform isn’t just about improving returns, it’s about giving families and investors a framework that endures.
Investors gain:
✓ A system that compounds instead of resets
No more selling winners.
No more losing equity to taxes.
No more remaking your portfolio every few years.
✓ A simplified plan for heirs
No 1031 pressure.
No management stress.
No operational complexity.
✓ A stable income engine for decades
Whether for retirement, legacy, or ongoing wealth creation, Permanent Capital creates financial predictability.
