Susan's Scoop

The Great Investment Dilemma: When to Hold, When to Let Go

I’ve been facing a decision lately that many investors (and homeowners) can probably relate to: Should I sell my property at a loss or keep holding on?

Our short-term rental cabin sits just outside Pigeon Forge, in the Smoky Mountains of Tennessee. We bought it during the pandemic-era boom when vacation rentals were selling like hotcakes and vacation rentals were the fad of the moment. Since then, the market has cooled, interest rates have climbed, and new cabins have popped up on every hillside. It also isn’t set up well for our family anymore now that our boys refuse to share a bed.

After 9 months on the market, we just finally received an offer - one that would let us walk away clean but would also mean selling at a loss of over $150,000 from our original purchase price. 😭

It’s the classic investor’s dilemma:

Do you sell now and stop the bleeding? Or hold out, hoping the market rebounds, and cover the ongoing costs in the meantime?

With debt payments, utilities, taxes, and capital expenses, it costs around $35,000 a year to keep the cabin running. The good news? After re-listing it as a short-term rental this summer with AirBNB (and managing it myself again after a horrible experience with a property manager), it’s finally bringing in almost enough to cover those expenses.

So we’re basically at break-even - not losing money, but not really making any either.

I don’t want to sell at what could be the bottom of the market. The Smokies are one of the most visited national parks in the country, and tourism tends to be stable since it’s a popular driving destination for the entire southeast US. Property values could potentially tick back up as interest rates drop and the market stabilizes. I would never encourage my clients to sell their stocks during a big downturn, so I feel like I should at least follow my own good advice!

And despite selling at a huge loss, we also will be looking at a large tax bill on the sale thanks to depreciation recapture, which I wrote about previously here (when we thought we could at least get $465k for the cabin, ugh).

But holding also carries risk. Oversupply, changing regulations, a couple of bad guests, maintenance issues, or even a natural disaster could tip the balance quickly. Or Dolly Parton could die and send that whole region into an economic tailspin (Dolly must live forever!!). And there’s the mental cost of hanging onto an asset that requires constant monitoring, decision-making, and low-grade worry for very little in return.

So do we sell and lock in the loss, or keep hanging on for dear life hoping for a recovery?

Sometimes the hardest financial choices aren’t just about spreadsheets and return on investment. They’re about energy, peace of mind, and timing your next season of life.

I’m sitting in that uncomfortable in-between space where both options make sense in different ways. Selling now would simplify life and free up capital, but it would also lock in a loss that feels premature. Holding on might give the market time to rebound, but it also keeps us tied to an unpredictable asset that demands attention and cash flow.

If you’ve ever stood at a similar crossroads, you know how tricky it can be. No option feels completely “right”.

We have 36 hours respond to the offer, so stay tuned! 😱

What I'm Reading

📕 The Serviceberry – Robin Wall Kimmerer (book)

If you care about how we live - not just how we survive - this short book will hit you in a good way. It’s a good reminder of what’s possible when we shift from “owning and consuming” in a market economy toward “giving, sharing, caring” in a gift economy. It looks at what it means to have “enough,” and what we choose to do with our abundance - sell it, keep it for ourselves, or offer it to those around us.

Join us for free the first Wednesday of each month for an informative money conversation!

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Nov. 5 - Open Enrollment Edition: Your Health Insurance and Benefits Questions Answered​

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