Worst case, it gets outlawed in a town AFTER you’ve bought a place there & now you have to sell at a HUGE loss bc there’s no buyer demand once STR use is banned!

It was my worst nightmare. 

If you care what a Fannie Mae type underwriter will think (ie, you want a 30YF of some sort in the future), put it all on a single line, it's one single property, according to what I think you said.

. - what will you do, if one year after you sold your flip, you are getting sued by the buyer because of some defect or issue, real or imagined, known to you or created by a sub/contractor, or fraud (like, because you made the mistake to advertise your flip for sale with "everything new" and the buyer discovered you didn't change the entire plumbing) and the judge freezes all your bank accounts till things get sorted out?

The worst he will say is "no" and you either take it as is, or walk away. 

LLC is the most common, of course, but I think any sort of formal entity will do. 

Am I setting myself up for failure by not always putting in worst case scenario?

Thank you Mark - I also saw a lot on google searches explaining that the death benefit was sort of a 'floor'.Since this account has done so well, and is far above the original investments, then the higher value is what we will be getting, vs the lower death benefit.

Worst case scenario yes we need to have someone else do it. 

It also has Pittsburgh addresses broken down by ward.It is trivially easy to sum, sort, and filter this data to see the kinds of information you're asking about.