Boston is not STR friendly unless you live in the property.

Me and my fiancé are wanting to try and purchase new construction homes in class A to B neighborhoods (275-350K) and put 20-25% downs and live in them for 1-2 years while we save another down payment and then eventually move on and make it a rental.We are not looking to scale rapidly.

I am now back to living in Texas and looking to start making deals again!

Where do you live now?

Are you focusing on a long term rental, medium term rental (30 days to 6 months), short term rental, or a live in house hack? 

Used to code for a living way back when, but now I've been swinging a hammer in construction for almost a decade.

local vs. virtual - if the greatest REI bookkeeper lives down the street from you, that means that your books only get done when they can physically get to you.

I failed to mention he doesn't have a job, he is solely living off this lump sum which I thought was fine considering all the great references I received. 

their bookkeeping software leaves a bit to be desired though, i always have trouble connecting my bank accts so i just manually upload the file monthly now. i'll live. i like how simple it is. with RR tenants can pay through the app, they get reminders, you can manually send reminders, they can make partial payments throughout the month, you can pay $5/unit to have their on-time payments reported to the credit bureau to help build their credit, you can do apps and background/credit/eviction report on there.. and yeah in MA there are just so many stipulations around how security deposits can be used i'd rather just not even deal with it. 

I noticed you are living in a duplex since you mentioned one side being rented out and you’re living basically rent-free.