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?

[Don Konipol]

Quote from @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?

Your decision is right on target - I 100% agree.
I “adjust” my investment portfolio ALL THE TIME - or at least contemplate it.  First, since I can remember, I always tried to maintain an overly cautious amount of $ in cash liquidity so (1) to meet ANY “contingencies” and (2) to be able to take advantage of rare opportunities.  When the “cash stash” was depleted I would figure out a way to add liquidity - sell a property, obtain a cash commission, take out a low interest loan on a free and clear property, etc. 

About 8 months ago I decided that the deals I was seeing had much greater profitability with less risk than the deals I had been seeing since 2001.  So I placed a low cash flowing high equity property I owned on the market, sold it for $670,000 last month and put the cash in reserve.  I already invested $250k in two notes yielding 17 and 18%, and looking seriously at a $250k short term play with minimal risk that has an expected value annual return over its max 24 months of 35% per year!   If that doesn’t pan out I may invest the $250k and some of the rest in REITs currently selling at 20% less than net asset value and paying dividends of 7.5% + . 

The thing I see in your investment philosophy where you might want to change (or not depending on your comfort level, expertise, and time) is instead of accepting any property investment as a long term given, seek out opportunities that offer higher returns.  Over 45 years investing I attribute 40% of my net worth to the power of the real estate investment itself, and 60% to “opportunistic” portfolio repositioning.  So, I’m NOT the guy that makes money turning an underutilized office building into residential trial apartments, or the guy that takes a piece of undeveloped land and develops it.  I “add value” merely by identifying and investing in properties, notes, and partnerships where the risk adjusted return is greatest.  Also, I “create” many of these situations through negotiation, creative deal making, and realizing that real estate is actually a “bundle of rights” that can be sliced, diced, and distributed each to the highest bidder.  

Anyway, you can do it in small steps.  Just realize that there’s a ton of opportunity out there; people are creating 8 or 9 figure net worth from virtually 0 as we speak, while most investors are satisfied with a 5% cash flow.