Not only is it a good way to identify goals, but I also think of it as an inexpensive way to spot weaknesses in my plan, identify false assumptions, and develop contingencies for the unexpected.

I've also used REI Hub for one client but the functions took more than twice as long to complete and the reporting feature is weak compared to QBO.

If it is chronic, tell them it isn't working out and suggest they find another place to live.  

Having a bunch of wealth locked up in an asset class with weak liquidity and high transaction costs has some real downsides. - Should move my properties to one or more LLCs, despite the tax headaches and increased annual transaction costs, or is a large umbrella liability policy achieve the same thing?  

It sounds like your market is rather weak so you will probably end up eating some TI's (tenant improvements).

How many times should I set up a meetings for us to review progress and improve on weaknesses?

It's easy to see what you want to see when it comes to family but being on honesty with yourself about their strengths/weaknesses as well as the strengths/weakness of your relationship is of utmost importance.

An investor owning in a weak suburban area might have fewer options to sell than a major metro such as Austin Texas where many investors can fly in and see the property.Austin Texas is ranked one of the hottest investment areas in the country.

Having $80K in bad debt, and then piling HELOCs on top of that to buy more real estate puts you in a position of financial weakness, should the markets even have a hiccup, or things go unexpectedly. 

Its not for those with a weak stomach though, the capital required can be daunting.