I didn't like QB because it isn't specifically for real estate.

There is no 1:1 troubleshooting that is really specific to your concerns.b.

I'd imagine that it is quite location specific as well, so I'd suggest poking around a bit on HipCamp as if you were a camper, and see what's around you. 

Maybe it might be different in your market, but at least here in CA, no real estate agent is going to refer  a client slow poke big bank unless it’s specialized bank offering a specific program that caters to the needs to the borrower.  

Do you have a specific market in mind for your first property?

I always make sure that the draws are commensurate with the amount of work (and specifically the trade) performed to date.

Insurance is done with a carrier that allows for undergrads (usually Foremost).Re: legality, this is specific to the town.

Newbie here- I haven't identified any specific assets yet but I'm looking at 4plex or smaller.

BP also provides state-specific leases to pro members.

Your worst-case scenario (not specific to MA) would be having to sue to get them out as a holdover, but this is really reserved for worst-choice scenarios when owners choose the first renter or don't do any due diligence.