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.
A business owner was selling a privately held business and personal residence in South Carolina in the $2.5M–$5M range. On a conventional sale, the projected combined federal and state tax fell in the $1M–$2.5M range, a large share of the transaction lost to tax, cutting the seller's liquidity and reinvestment options.