I have done flip and turn, rehabbing, hold and rent, 1031 exchanges, property management, property peservation, BPO's, AITD's, wraps, land contracts, subject to's and loan assumptions.I wish this site had been around 20 years ago.

There is the possibility he's looking to trade up (1031 Exchange) which would be a good thing but DO your research on this property.

Ideally I will 1031 exchange and not pay taxes immediately on this profit.What am I missing?

Many focus on the emotional acquisition (especially seen with 1031 exchanges) so heavily it obscures that - depending on the type, eg. multi which you referenced - some have a much longer "hold" period.

This is one of the best sources for Investors and Real Estate Professionals to network and research and exchange information.

The more equity you have, the bigger the additional lump sum payment can be from a HELOC thus reducing amortized interest in exchange for simple interest.  

I try to post topics that will generate an exchange of thoughts, different viewpoints or outright disagreements.

No reason to be nervous abouth a 1031 exchange.

So I see no problem in future, only it must be global on each stock exchange.

Your best bet for getting cash on either of these deals is to 1) get them under contract and flip the contract to someone else, or 2) get the car lot seller to give you $20K in cash and the property in exchange for a $190K note.