Occasionally there are some that don't ask 1000 questions and are pretty self sufficient, just trying to maximize their time and network, so those may get some consideration. 

@Zaid Mahmood I'm not in those areas but consider myself pretty experienced in the LP space.

Since MA has a pretty high price point I would suggest house hacking. 

Send via certified mail.As for your post-mortem, assuming the money is gone and it is not worth your time and effort to keep fighting for it, I personally am pretty biased against crowdfunding sites like SmallChange, CrowdStreet, and others.  

You can type in the properties address and it pulls data from airbnb and other short term site to give you from what I've read a pretty accurate estimation of Occupancy rates and income.

We have a builder in Charlotte that constructs multi family and the numbers are pretty good.

That's pretty harsh. 

My issue with Bako is that the cheap houses are in pretty rough areas, and are likely to remain cheap.

1014 is pretty cool !

However, cancellation during stay is pretty unique situation and I don't think airbnb app is equipped to handle those cases well.