If you had 20 units at $66/door you at least have some substantial cash-flow to handle those issues and everything doesn't break at once. 

At least 50 percent of the assets of the business, valued at cost, must be invested in real estate which is managed or developed and with respect to which such entity has the right to substantially participate directly in the management or development activities.b.

If the back unit can get a GRM of anything substantially less than the market rate GRM then it’s a good idea?

That being said, I'm close to being done with the corporate 9-5 job and would really love to jump into it so I've been debating asking a wealthy uncle to borrow a substantial amount of money in order to get started. 

Checkout 72t  distributions especially SEPP ( substantially equal periodic payments) and see if that is an option for you.

Personally, I would not even mention it when getting quotes, unless you get a contractor via the website in the first place.The only way to know whether you are getting a good deal - unless you yourself are in construction - is to get at least three quotes from qualified and licensed contractors.Just make sure that the quotes are something more substantial than just “Repair X.

Secondly, an LLC selling to an LLC with substantially the same membership would not pass muster as being unrelated parties and if you get into related party issues....well let's just say you don't want to get into related party issues!  

I will be there when the market dictates they sell at a substantial loss.

They are willing to take a blended method and review market rents and raise that value if they see that market rents are substantially higher.  

But I'm ready to make the shift and think there is some substantial growth potential.