Selling a business, rental property, or other large asset triggers a range of tax consequences, including capital gains tax, depreciation recapture, and the net investment income tax, that can result in a significantly larger bill than most sellers anticipate. Tools like installment sale elections, deal structure adjustments, and strategic closing timing can reduce that exposure, but most of them require action before the transaction is finalized. A conversation with your CPA before you enter active negotiations is the most reliable way to protect your after-tax proceeds.