*My goal is to be able to confidently, accurately and quickly be able to pull the trigger on some deals.* Now, I understand I don't know what I don't know.

So before I pull the trigger (and still saving $ for it now), I'm analyzing lots of properties and crunching numbers.

You could always issue a notice to vacate on one of the units "for purposes of renovation", then update it, raise rents to market, then issue notice on next unit, etc.Even in tenant-friendly MA, hopefully that is allowable without triggering any fair housing violations.

The good news is that if you converted a 4-unit rental to a primary (1 unit) in order to get the Sec 121 exemption, you could use a 1031 exchange for the other three units.Live-in multis get complicated when it comes to this stuff, so I would definitely recommend you speak to a prop before you pull any triggers on this strategy. 

IFrom what I am seeing I can flip but potentially that would cost 40% as it would trigger UBIT.

Very few roads in and out, and if your not familiar with it it’s very easy to get turned around.Right now I’m thinking of pulling the trigger on a rental property in one of the towns in the area.

I am from Portland and recently starting out myself, I have everything lined up to pull the trigger just looking for a deal now. 

Everyone has it inside of them but something has to trigger it. 

For now, I'm focused mostly on analyzing deals in the hopes that I will be able to pull the trigger when I find a decent 1st investment after my wedding.Thanks for reading, Brian 

Then just be patient and ready to pull the trigger on a homerun small unit apartment or flip.