Updated over 19 years ago on .
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Which is better to Sell now or later?
Our dad is no longer living in his home because he is in assisted living. The home is paid for and there is currently a tenant in it. The income is helping to offset the expense of assisted living. Is it better for him to sell it now before the 2 out of the last 5 years requirement expires (for the capital gains exclusion) or to just leave it as a rental and sell it much later after he's gone with a stepped up basis. The property is in a trust. Btw, he has enough savings where he doesn't necessarily need the rental income this late in his life.