The full $500,000 capital gain would be exempted from tax under the principal residence exemption. Since they had no taxable capital gains in the current and prior three tax years, the $75,000 net capital losses can be applied without adjustment to offset pension income from 2025 and 2026 (i.e., $37,500 in each year).
For the target, a stock sale is usually a nonevent from a tax perspective. The buyer in a stock sale does not get a step-up in tax basis in the assets that comprise the target company, and thus is not able to increase their depreciation and amortization deductions in the same way as in an asset sale.
The short answer is that a stock sale is better for you, the seller, while the buyer benefits from an asset sale. But, since we're talking about the IRS, there are infinite variations and complications. As such, you will want to get professional tax and legal advice before proceeding.
Disadvantages of Asset Sale The seller is subject to a double layer of taxation. Transferring assets may be more complicated. Agreements tied to certain assets may need to be renegotiated.
In an asset sale, the ownership of these acquired assets would change hands, with the buyer negotiating separately for each asset. In a stock sale, ownership of such assets does not change hands in the same way. The target still retains its ownership typically, even if the target has a new owner.
Almost everything you own and use for personal or investment purposes is a capital asset. Examples of capital assets include a home, personal-use items like household furnishings, and stocks or bonds held as investments.
Stocks are financial assets. They're not real assets. A financial asset is a liquid asset that gets its value from a contractual right or ownership claim.
Generally, any profit you make on the sale of an asset is taxable at either 0%, 15% or 20% if you held the shares for more than a year, or at your ordinary tax rate if you held the shares for a year or less. Any dividends you receive from a stock are also usually taxable.