If something goes wrong the person can enter a bad spiral.  

Whoever you talked to at the HOA might have had an agenda or may have given you bad info so I would double check.Offering seller financing may help by increasing your pool of buyers.

Will be moving soon to a (annoyingly) HOCL area for career and to be closer to family.Based on career/projected income, was offered a 0% down, no PMI, owner-occupied option (Rate is ~4.8%) from a bank we have a relationship with.

Not necessarily who I want to have move in.I thought the advantage of the MTM was if I had bad renters or renters who didn't like to pay it would be easier to get rid of them, but there are ways to get them out without the MTM if it's THAT bad.

I would be a bit concerned about the area due to the low rents and price, but strictly based on the numbers it doesn't look bad.

If you do a straight subject to, they won't have any standing.That being said, a lease does give a tenant some rights, however the "equitable interest' I believe you are referring to will not give you much standing in court if the deal goes bad, no matter how much in repairs you did. 

It's fantastic that you're working hard on the side, and two months working after hours isn't bad at all!

Which is a 9.6% CoC return, which is not a bad return.

Do you have the cash reserves if something bad happens or you have to evict because the tenant isn't paying? 

A sale will extend the time to get the house boarded up or renovated.I am not familiar with Probates and it seems they have let this house get into a bad position.