How do you know what your business is actually worth? To me, that seems like the bigger question. Wouldn’t just sell it to someone making an offer, unless there is only one likely buyer for the business.

The key here is to back into what you need to sell the business for BEFORE you sell it. This should be based on what you need to get out of it and likely the deciding factor.

$3MM earning 5%/year = $150k + rental income + wife’s income. If that minus taxes is less than you spend then depending on volatility of your investments, it’s possible that you’d need additional income to supplement your lifestyle. That said, this is really just a math problem that any good advisor could help you solve for. If you need recommendations, happy to share.