working short sales takes talent, not for the untrained or the impatientI would talk to a 10+ yr vet of short sale negotiations with the major lenders.

While this doesn't mean that you shouldn't keep your eye out for other deals that are on the website, preparing for future deals puts you ahead of the curve from the untrained bidder.

I've considered cash out refi or HELOC, plus my cash on hand, but to my un-trained eye, it doesnt look like that will get it done. 

Get lawn cut, bushes and tree limbs trimmedFresh smellSpend rehab money where you get the biggest bang (i.e. bathrooms, kitchen, paint, flooring, fixtures, etc) vs roof, condenser, hot water heater, etc (assuming they are in at least okay condition to the untrained eye)

We are encouraging weakness and, like an untrained emotional support animal, it will come back to bite us as a society.

I have very little expertise when it comes to foundations but, to my untrained eyes, it appears to be a legitimate attempt to fix the problem long term.

Three year roof - to my untrained eye based on my own roof experience, I'd say yes.

Not really any work that needs to be done from what my untrained eyes can see.

You can certainly find lenders and products which will consider the rental income for future loans.I don't have much knowledge of LLCs, but this doesn't sound like the right move to my untrained perspective. 

There was a final walk through of the property, but, as I didn't know about the pipe burst, I didn't know to look for water damage (even after I was made aware of this problem, with an untrained eye, it's hard to notice issues besides some sagging drywall and water drips on parts of the wall) and some part of the wood floor coming up outside of the bathroom door.