Tied Up in Property: Planning Retirement and Liquidity for Margo Sinclair

Assessing the Portfolio, Property by Property

The first step is clarity. We evaluate each property across multiple dimensions: fair market rent, ongoing maintenance costs, location-specific tax exposure, and potential sale value. That allows us to separate the “keepers” from the “sell soon” list.

Margo doesn’t want to fire-sale the portfolio, so we build a phased divestment plan—selling select properties in the first few years of retirement to create liquidity while minimizing year-over-year tax drag. The properties she holds onto are transitioned to professional property management, so she no longer needs to be the first call when something breaks.

Creating Liquidity Without an Overwhelming Tax Bill

Selling appreciated real estate comes with tax consequences. We work with her CPA to develop a multi-year strategy that spreads out capital gains and explores options like installment sales or targeted charitable giving. The goal is to convert equity into flexible assets—without triggering a tax event that derails her cash flow or long-term plan.

We also revisit depreciation schedules and ensure records are up to date so we can maximize cost basis step-up opportunities and avoid unnecessary taxation.

Reframing the Inheritance Conversation

Margo initially hopes to pass the properties on to her children—but after candid family conversations, she realizes that her kids aren’t interested in being landlords. Rather than leaving them with a logistical burden, we explore which, if any, properties hold sentimental or investment value. For the rest, the plan is clear: simplify, sell over time, and convert value into more manageable, liquid assets her children can use on their own terms.

This clarity doesn’t just serve Margo—it gives her children peace of mind and avoids the friction that often arises when heirs inherit real estate they didn’t ask for.

Planning for Continuity and Peace of Mind

One of Margo’s biggest concerns is: Who takes over if something happens to me? Managing 14 properties, multiple bank accounts, and a patchwork of LLCs can be overwhelming—especially for adult children with no real estate experience.

We create a centralized financial dashboard that gives Margo and her family clear visibility across all assets. Beyond the numbers, she works with our dedicated advisory team that knows her full financial picture—not just her portfolio, but her goals, values, and decision history. That consistency gives her confidence that if something happens, she isn’t leaving her family in the dark.

We also bring her adult children into selected planning meetings—so they understand the strategy behind key decisions and know who to call when the time comes. Together, we’re building not just a plan, but a shared understanding that can carry forward across generations.