The right answer hinges on what you'd do with the proceeds and how the taxes shake out, so start there. If you sold, would you reinvest in other real estate (possibly through a 1031 exchange), sit in cash waiting for a better entry, or use the money for something else entirely? That plan drives everything downstream. Then the tax picture. If the home has been your primary residence, IRS Section 121 lets a married couple exclude up to $500,000 of gain (up to $250,000 single), but only if you've lived there at least two of the last five years. Converting to a long-term rental eventually burns through that window, so waiting too long can forfeit the exclusion. Confirm the timing and current rules with a tax professional. If you're leaning short-term rental, add these to the list: - HOA restrictions and your city's short-term rental rules, which keep changing. - Whether you actually want the operational load. An STR runs closer to a small business than passive landlording. With this much money on the line, sit down with a professional who can walk the full financial and tax picture with your specific numbers before you commit either way.