Paulo Aguilar, CFA, CAIA

Multigenerational estate planning is not only about transferring assets. It is about transferring outcomes.

A failed 1031 exchange is not uncommon, but it is rarely anticipated. Identification deadlines, financing delays, buyer withdrawals, and documentation errors can all derail an exchange. When that happens, investors are left facing immediate tax consequences and limited options.

Most failed 1031 exchanges do not fail because the investor misunderstood the tax code. They fail because timing, execution, or external disruption narrowed options faster than expected. Identification deadlines arrive whether replacement property decisions are complete or not.

Selling a commercial property is often described as a liquidity event. From a tax perspective, it is better understood as a recognition event.

Liquidity is one of the most important, and most frequently misunderstood, aspects of Delaware Statutory Trust (DST) investments.

Delaware Statutory Trusts (DSTs) are often discussed in the context of 1031 exchanges. Less often discussed is how they are taxed during ownership and at exit. That gap leads to unrealistic expectations and avoidable confusion.

When families inherit assets, the most important tax question is often misunderstood. It is not what the asset is worth today. It is how the IRS measures the gain when that asset is eventually sold.

For many business owners, valuation is assumed to be a function of revenue, margins, and growth. Technology is often viewed as a supporting detail rather than a value driver. In exit scenarios, that assumption can materially misprice risk.

Delaware Statutory Trusts (DSTs) are often evaluated one offering at a time. Investors review a property, a tenant, and a projected return, then decide whether it fits. That approach misses a larger question that matters more over time: how different DST structures interact inside a portfolio.