No survey pits “rent it out” directly against “sell it and invest the money,” so this pairs the two closest measured regrets. About 40% of residential rental owners wish they’d never started investing in real estate (Clever Real Estate’s 2024 survey of 764 investors), against about 25% of recent sellers who regret selling because they miss the home they gave up (Clever’s 2022 survey of 1,000 sellers). On those proxies, keeping-and-renting is the more-regretted path — the opposite of the intuition that selling is the move you might kick yourself for later.
The reason keep-and-rent regret runs high is that landlording is not the passive income it is sold as. In the same 2024 survey, 56% of owners had already had to evict a tenant, 61% were still chasing missed rent every month, and 87% reported some regret about their investment decisions. The NBER study of landlords’ own lease ledgers puts a price on the hassle: filing a single eviction costs the equivalent of two to three months’ rent, and nonpayment is common enough that many landlords tolerate months of it before acting. Against that, the seller’s regret is quieter and more emotional — missing a home — rather than a recurring operational drain.
Read the gap cautiously. This is a proxy pairing, flagged as such: the two numbers come from different people surveyed in different years, the seller figure includes forced moves that mix circumstance with choice, and the investor sample leans toward heavily-invested owners who may regret more than a one-flat landlord would. It also says nothing about the money — whether renting out or selling-and-investing wins financially depends on rental yield, local price growth, and what the sale proceeds earn elsewhere, none of which a regret rate measures. The Gilovich pattern (holding-and-managing regret accumulates while the sold home fades into a wistful memory) fits the direction here, but the evidence is indicative, not a head-to-head test.