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 residential real estate portfolio in Illinois in the $20M+ range. On a conventional sale, the projected combined federal and state tax fell in the $5M+ range, a large share of the transaction lost to tax, cutting the seller's liquidity and reinvestment options.