He must have thought he would have more time or something - based on the tales of "people living in homes rent free for years!"...

Here's a little backstory 1 yr and some couple of months ago, I was at the Joint Base Lewis–McChord library in Washington State.

The speaker Doug Clark showed pictures throughout the weekend about his cars, the houses, the money, the trips, more cars, but also kept selling CONSTANTLY his "Diamond Program" that apparently is based in Utah.

Based on my 5min searching on apartments.com in Lynhurst, I noticed more than half of the SFH listed had AC so I would definitely pull the trigger. 

VA allows you to carry 2 VA loans with specific circumstances (which you would qualify under based on what you wrote) but you can only have one loan below $144k and one above $144k (or somewhere close to that amount).  

The point was how low of a CAP rate would be needed to achieve that goal based on the starting point of available funds.  

What I might suggest is to have a quick 1 page or 1 paragraph "example ballpark job quote" pitch for 1-3 small example projects for them to respond to based on something within their field/trade.

., figure out their typical useful life, and determine how much should be set aside each year based on the current replacement cost.  

Eventually would either gift his amount back or would gift 50% of units later on (but based on a merit agreement).

You should refinance based on appraised value so find the bank that does this for you.Hence, my questions above regarding due diligence on real property value and additional ways to value-add to increase the properties value.I hope this helps.