When to Sell: Navigating Between Long-Term Wealth and Short-Term Needs

[Gregory Schwartz]

I’ve been reflecting a lot lately on the difference between being wealthy on paper and feeling financially secure day-to-day.

We currently own several rental properties in Bryan and College Station, TX—most of which don’t cashflow much, but they at least break even, occasionally allowing us to make improvements like new siding, stairs, or converting a unit to an Airbnb. I’m genuinely proud of the portfolio we’ve built. The properties are in great shape, the market fundamentals are strong, and I firmly believe that over the next 20 to 30 years, the equity we’ve built will turn into a major asset for our retirement.

I recently played around with a retirement calculator and the projected number at age 65 was way higher than what we currently live on—which was exciting… until I looked at our current financial position.

Despite all this long-term equity, we’re feeling squeezed. We don’t have a fully funded emergency fund (we’re not even at 6 months). We need about $15K for an important project on our personal home. And while four of my rental units have received new HVAC systems recently, our own home still has a 30-year-old unit barely making it through Texas summers.

I’m also self-employed, so our income isn’t always consistent—it’s seasonal and can fluctuate significantly. All of this led us to a tough but necessary decision: we’re going to sell one of our rental properties.

It’s our least favorite one. The equity is there, and the sale will allow us to:

• Fully fund our emergency savings

• Knock out the $15K personal project

• Shore up our financial foundation so we can breathe a little easier

This isn’t a move made out of panic or desperation. It’s a strategic rebalancing—trading a piece of our long-term vision to strengthen our position today.

I’m sharing this because I think many investors—especially those of us early or mid-journey—face similar tension between long-term wealth building and short-term financial realities. Sometimes the smartest move isn’t to buy more, but to adjust your current foundation so you can invest from a position of strength.

Have you ever sold a rental to fund your personal financial stability?