Tax Stategies for a 1M+ real estate sale

[Shadonna N.]

I know an owner (very old school) who is ready to retire and liquidate his portfolio.  He has a few buildings in DC valued at over $1M .  He has already started to sell off some of his properties.  He does not employ any tax strategies and pays the maximum tax when he sells.  Properties are paid in full.  Guy is very old school, no debt, straight deals.  We are trying to offer suggestions for him to minimize his tax obligation without making things too complicated.  Could a trust be used?  What about an exchange?  Is it always real estate for real estate?  Any ideas?