My boss sold his house (lucky guy) at a price well above basis and over his $250,000 exclusion. He has a lot of stock losses this year. Can he use BOTH long and short term investment losses to cover his long term capital gains on his house? Any additional ideas on the best way to reduce taxes on this one-time large capital gain event? He is over 70 years old and the house was located in Hawaii. Thank you.
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