I guess once again Florida is behind the times.I agree with many (if not all of your points) for your markets, but for most of the eastcoast online auctions are in place and the big players will certainty work a deal with a title company to get a good deal or maybe free for their work.Now, this leaves a big market of investors trying to wedge their way into auctions.I guess the main points of contention here as i see them are 2.1.

Want to up my game.Started searching college towns, commuter towns outside of Boston (Manchester,NH , Providence, New Haven) trying not to be fearful of leaving my comfort zone ( Boston) which is highly priced as you know.Well, I found I very quite town in NH , nothing special about it , no big business, no huge draw but the population is holding its own, low crime...just a quaint town.This particular property is 8 unit with 6 add'l storage units & 2 garages ( those aren't bringing in revenue as of yet, not utilized) All are in good shape, not worn or old. 

Or leave them under their each individual mortgage?

I was looking at the refi option because the amount I can get for rent would just about cover the new mortgage on our primary, leaving us almost no money out of pocket for living.

If the custom in your area is for only nine month leases, leaving you to scramble for short term tenants during the summer, it will be harder. 

Moving because of work, increase in family size, leaving a jointly owned property.

I don't plan on leaving NYC so I am beginning to look for out of state investments.

Year 2 buy another BRRR or you leave your $150000 in one house.

Really the best way is to just use financing that allows for LLC which is probably a commercial loan, cash also works.If you have a residential loan (30 year fixed for example), then probably just leave it in your name

The first one we had some how figured out how to magically have all the tenants leave in 3 months.