A temporary absence due to special circumstances, such as illness, education, business, military service, or vacation, won't change your main home."

Kindly tell her you don’t want nor need to hear the details or circumstances surrounding the separation / divorce .

If it is FHA definitely not, in other circumstances the seller is probably not going to be a fan of your offer because you would be asking a stranger to borrow probably $20,000 or more.

I have a family member who will loan me money to start set up my LLC as well as for other things, but they will not under any circumstances loan me money to purchase more education due to all the education my late wife and I have already purchased, and they check my purchases.

If they purchased through that program they are required to bring the house up to living conditions within 6 months of purchase (9 months in certain circumstances).

How about:-Offer to sell him the house/lease option it to him, possible at a favorable price (to you, since he seems to love this house)-Get something in writing that allows him to continue his "hobby", but allows you to approve work actions AND clearly states you will not be reimbursing him or paying him in any circumstance for improves he does decide to implement on his own.   

This is clearly specific facts and circumstances based but I’m curious to know whether based on historical returns you would have decided on a go vs. no go on a property when you were on the fence due to these variable assumptions such as repairs and capex and your historical experience is tipping toward a lower % than the assumptions being used when analyzing.

I'd write the HOA and ask if they'll at least split the bill with you considering the circumstances and the fact that the repair that would be their responsibility is actually fixed. 

But there could always be specific circumstances where a shorter (or longer) hold period are appropriate.In your case an unsolicited offer to buy at an advantageous price would certainly provide a great defense if ever questioned. 

However, even then there are still people who do have circumstances where they may be motivated enough to do a terms deal.