I have a question about capital gains. [View all]

[font color="navy" face="Verdana"]A friend of mine is one of the old-school Republicans, a very decent guy who's fair and even-handed. We've discussed politics a number of times and he says he could be a Democrat because he agrees with most of the social justice platform. The reason he remains Republican, though, is because of "Democratic red tape" and some perceived unfairness in the tax code.

Specifically, he wants to know why, if he sells a small apartment complex he owns (valued at <$1.5 million) as his "retirement," he can't get a one-time deferment of capital gains taxes in the same way a homeowner can get a one-time deferment on the sale of their home. He thinks this should apply to selling any commercial property or business valued at <$4 million, a once-in-a-lifetime exception.

I started trying to research the law and was in way over my head. Are there any tax experts here who can answer his question? He's really willing to abandon the GOP if he can understand this, since he blames Democrats for the "unfair" lack of exemption in such a case, and is otherwise on board with most of the Democratic platform.

Thanks in advance!