You should have started the process to collect as soon as rent was not received on time.Most landlord selling simply walk away from the loss.

It just seems like it's so dangerous to even attempt a friendly conversation about someone else's financial situation because of the potential for stepping into a hot mess legally.

It's called "Subject To" but that simply means taking over somebodies loan.

Personally I like the idea of having a few properties owned outright , simply for safety / risk reduction to keep the wheels turning in tough times and there will always be tough times or massive expenses if your in this game long enough .

Have you figured out if you'll be acquiring distressed properties and then fixing them up to rent or simply buying fully renovated homes?

I'd recommend Stamford, simply because of the ease of commuting into the city.  

Originally, I had intended to simply have them transfer the deed to me subject to the existing financing or simply buy the house from them for what is owed on the house using a short term hard money loan, but the more i think about it, the more it might not be a good idea for any deed transfer.

There simply isn't.

😎I recently saw 5 Flights Up. ehhh, it was just OK, but the entire movie did center around an older couple and their attempts to sell a NY property that they lived in for a very long time.

You simply need to get an explanation.