HOA can't foresee your roof issue until you report it.If there was a roof leak and you reported it to the Hoa in timely manner, but they did not address it, which in turn kept leaking with subsequent rains causing damage, then I believe  you may have a claim.The roof has been repaired so get a quote to repair the ceiling.

Is this a person who is, from here, going to turn their life around from the desperate situation that they find themselves in right now, such that they are willing to take a Subject-To deal? 

He even asked his assistant if he could get the chat turned on.

Previously though most of the MTRs stayed 3-6 months, so we've averaged about 3 turns per year, with about 1 week between tenants. 

Based on the info in your post, my recommendation would be to turn these assets into well oiled machines and max out their NOI.

As others noted, there is no limit to DSCR funding other than your ability to produce enough liquidity for down payments, closing costs, and the required reserves post-closing.

In the end we had to pay to turn the space back in to a white box/shell and closed with basically zero physical assets.

And what is your price range and are you looking for turn-key properties or something along the lines of a "fixer upper"?

They have a lot of experience, over 50 years of it, lol, so I would say they’re a proven choice for turning retirement funds into real estate investments.Simply mention you’re a BiggerPockets member, and they’ll provide a tailored experience.

Unless you have discovered some hidden jewel, the traditional second home locations have all turned stale.