Paying 15–20 percent long-term capital gains with minimal effort often beats earning taxed-at-37-percent real estate income that requires time, stress, and active management.

I’ve had a few conversations lately with people who just sold their primary residence and immediately started stressing about how much tax they’ll owe on the gain.Here’s the part many homeowners don’t realize:Section 121 of the tax code allows you to exclude up to $250,000 of gain if you’re single, or $500,000 if you’re married, as long as you meet the ownership and use requirements.For a lot of people, that means no tax at all on the sale of their primary home.Of course, details matter — how long you lived there, when you moved out, prior rentals, improvements, and timing can all affect the calculation.

Their operational controls, vendor management, financial accuracy, and on-the-ground execution were consistently lacking, creating financial risk and unnecessary stress for owners.

I found it helpful to look at markets across multiple tradeoffs instead of treating any single metric as decisive.As a simple illustration, consider two geographically close Midwest markets — Cincinnati and Columbus — not to declare a winner, but to show how different lenses highlight different strengths.Common heuristics investors tend to reference:Cincinnati: lower median home price, lower typical rent, often meets the 1% rule, moderate historical appreciation.Columbus: higher median home price, higher typical rent, rarely meets the 1% rule, stronger historical appreciation.These signals are useful for understanding entry price and basic cash-flow potential.Signals that surface broader tradeoffs:Cincinnati: higher rent-to-income pressure, more concentrated employment base, slower liquidity (days on market and inventory), lower structural friction.Columbus: more resilient rent-to-income, more diversified employment base, faster liquidity, moderate structural friction.This second view doesn’t predict outcomes or replace deal analysis — it helps explain why similar-looking markets behave differently under stress, growth, or different strategies.All of this is relative, not absolute, and weighting depends entirely on goals (cash flow, appreciation, balance, risk tolerance).

It's gonna be stressful and you aren't going to find a perfect deal, that's what weeds out the tire kickers and spreadsheet warriors- risk.

A few questions that go a long way are:• What’s the real cost once you include points, fees, and any extensions• How quickly they can close and what they need from you to keep things moving• Whether they’re open to a seller carryback or subordinate financing• What the exit path looks like and if they’re comfortable with you refinancing into DSCR or bank debt later• What their process is if the appraisal comes in lower than expectedMost people forget to ask these and end up stressed later.

This is why it is stressed to have a contingency fund in your budget, but do you have enough?

And others that have been going bankrupt like Starcity were more because of COVID and ending in cashflow problems because of the decreased occupancies. 

If you have property in MO, I'd focus on building long term, trusting relationships there with professionals who have your best interest in mind so that when you do have an issue, they'll jump in and make it disappear so you can sleep at night.Sorry you are dealing with this- it's stressful and frustrating for sure, been there many times.

We run early screens one way, then tighten everything once we know the asset.If helpful, we’ve built underwriting templates and deal screens specifically to stress-test high-tax markets like MI and flag whether the problem is pricing, expenses, or lack of a value-add lever.