Start with whether you can carry both homes. If the purchase only works by selling, sell quickly and the rest is moot. If you qualify for the new home without selling the old one, and you're genuinely comfortable holding both payments, you have real options. Run the rental numbers honestly. Put the rent you could actually get against the full payment, estimate expenses aggressively and income conservatively, because vacancy, repairs, and upkeep have a way of turning a "positive" rental slightly negative. A property manager typically runs 6 to 10 percent of monthly rent if you don't want to be hands-on. Our guest Michael Zuber, author of One Rental at a Time, put it well: never keep an "alligator," a property you have to feed cash every month. When the home pays for itself, holding for the leverage, appreciation, and long-term income tends to reward you, and people rarely regret keeping real estate they could afford to keep. One tax point to confirm with your own tax advisor: the capital-gains exclusion on a primary residence generally requires you to have lived there two of the last five years. Convert the home to a long-term rental and you can eventually lose that exclusion, making the built-up gain taxable at sale. That timing sometimes tips the decision toward selling while the exclusion still applies. And if landlording was never something you wanted, or the cash is more useful elsewhere (paying down the new mortgage, another property), selling is a perfectly good call.