Selling a valuable asset in a high-tax situation can leave a seller with far less than the headline price. Federal and state capital gains, depreciation recapture, and the net investment income surtax stack up quickly. A pre-sale analysis looks at the whole picture before the transaction closes, when the outcome can still be changed.
An investor was selling a commercial office buildings in California in the $10M–$20M range. On a conventional sale, the projected combined federal and state tax reached the $2.5M–$5M range. Because the property carried substantial debt, tax plus debt payoff would have left the owner underwater, a projected net loss despite a high-value transaction.