I think looking to get face-time with someone who is experienced in this specific situation and market status would be really helpful to answer some internal questions and provide guidance and external motivation to make a decision and get moving. 

To explain the situation a bit better the 3rd party company is called Obligo, according to them once they receive the repair estimate from the management company they instantly pay them.

That being said, we have now run into a strange situation where I am not quite sure how to proceed.The tenant in question funnily enough happens to be my neighbor, as I own several units on the lot and for this reason, I have managed it personally over the years unlike other assets in our portfolio.

Jimmy, with you situation as stated, your options are limited. 

it's possible but unlikely. a great CPA who specializes in REI will be able to help you plan AHEAD for tax time and use different pieces of the tax code to your advantage, based on your unique situation, and ultimately save you way more in the long run. would you rather pay $750 to have a return done & get a $5,000 return, or pay $30 to have a return done and owe $5,000?

Maybe if he pushed a pencil he could have kept working a couple years I don't know.One of the problems with SSDI and other entitlements is that you can't pass rules to deal with every situation.

There are ways to deal with these situations, and it depends on the property and the lien holder, but it's possible to do some pretty incredible things if you are willing to invest a little more in legal costs to close the gap on your losses.  

It sounded like the team working on the loan wasn't motivated to close as the usual path on these situations is to find a solution with the sellers to get the loan done. 

I’ll update this post once I have an update on the situation.

The LLC is the business structure most use when investing in STRs.If you're extra worried about liability you could split the 3 properties into 3 LLCs but to me this seems like a situation of "If it ain't broke don't fix it"