It tries to do too many things and poorly at that.

Use caution when borrowing against your stock portfolio, especially if it's a high volatility portfolio comprised of individual companies.

You LP lost everything.Other ways, poor property management team isn't managing property well, and syndicator bought in tertiary market with only one or two managers available and no way to self manage.  

You'll have to keep escalating this to get it resolved as the national PMC you hired is probably using poorly trained VAs who don't know/care/authorized to fix the problem.What do you mean about the, "undisclosed maintenance markup fees"?

This is a fine needle to thread because at this size, you very quickly start competing with high net worth individuals who are seeking summer homes. 

So the question becomes based on their individual and personal tax situation what is the estimated tax burden they'd save? 

RISKSPrivate Letter Rulings There are three (3) Private Letter Rulings (“PLRs”) that address this 1031 Exchange structure, which are as follows: Private Letter Ruling Number 2014-08019Private Letter Ruling Number 2003-29021Private Letter Ruling Number 2002-51008PLRs can only be relied upon by the individual taxpayers that requested the PLRs.

Also if he hasn’t yet you should try to get him to read Rich Dad Poor Dad.

I'm excited to join this group of like-minded individuals passionate about real estate investing. 

Even in HCOL areas, adding an ADU typically does not make sense because developing a single small unit is the most expensive residential development that exists.Adding an ADU is a lot of work (probably more than a brrrr but with worse return), has poor financing options, typically adds less value than the cost of the addition, and detracts something from the primary structure even if it is just yard and privacy.Good luck