By Chase Keller, CCIM
“I’ll sell in a few years” sounds safe, but waiting often quietly erodes your net proceeds through increased costs, necessary capital expenditures, interest rate fluctuations, and market changes.
The real question isn’t “Should I sell right now?” but “What does waiting actually cost me over the next 3–5 years?” A clear side-by-side comparison of selling now versus selling later versus holding off until you’re ready to retire usually reveals a front-runner. Often, the “highest future profit” is not the most likely outcome.
I recently spoke to an owner of a 70-room franchise hotel in a smaller Midwest market. Good location, solid repeat business, nothing flashy—but it generated steady cash flow. He’d been thinking about selling for a while, but every time the market felt “good,” something came up: a renovation project, hoping interest rates would be better next year, and sometimes, simple inertia—”I don’t know where to start, and I’m too busy to do the research.”
Fast forward a few years, and the brand announced a large mandatory Property Improvement Plan (PIP) . The owner realized that the cost of construction had increased dramatically. Debt is more expensive than it was a couple of years ago. Now he’s forced to admit: “If I had sold when I first thought about it, I’d be in Florida by now. Did I wait too long?”
If you own a similar hotel, you’ve probably felt some version of this. The deal you thought you’d do “in a couple of years” keeps getting postponed, while the world doesn’t exactly stand still. Here are five things to keep in mind when this occurs:
As an owner, time is not your friend. What I see over and over with owners who are thinking about selling “someday”: their delays are certain to erode the market value of their property. Construction costs, labor, and brand standards rarely, if ever, get cheaper. A PIP that might cost $600,000 today can easily be $800,000 or more a few years from now.
Deferred maintenance quietly accumulates and reduces the property’s value in the buyer’s eyes. Roofs, parking lots, case goods, aging HVAC equipment, outdated furnishings—buyers notice, and they price it in when they make an offer.
Debt terms shift. Interest rates, prepayment penalties, and refinance options today may look very different in two or three years.
Your energy and enthusiasm will decline over time. Even if you don’t describe it as burnout, the hotel that felt manageable in your 40s or 50s can feel very different later, especially if you’ve gone through a couple of tough years. Unfortunately, there’s no flashing red sign that says, “This is the top of the curve—it’s all downhill from here.” There’s just a mix of brand demands, lender requirements, RevPAR swings, and emails from brokers like me asking if you’re ready to exit the business.
This isn’t about “timing the market,” which any experienced broker will tell you is impossible to do. It’s a question about how much more risk and capital you want to invest over the next couple of years on the chance of a better exit later.
Sometimes, later becomes never. For many hotel owners, “someday” becomes years of hard work and capital outlay without a clear plan for a return on the investment. Because I’m in hotel deals every day, I don’t think in terms of “now versus five years from now” in the abstract. Instead, I ask: “What are your real options from here—and what does each one look like on paper?”
Most of the time, there are three primary exit options: 1. Hold and keep operating, planning a sale “down the road.” 2. Sell in the near term, more or less as-is. 3. Invest, reposition a bit, then sell with a clearer story and cleaner property.
From there, it’s less about guessing the perfect market moment and more about understanding the trade-offs: capital out of your pocket, years of your time, and risk you’re holding on to versus handing off.
In the next post, I’ll discuss each option and its pros and cons.
