House Hacking - Duplex or triplex?

[Wendell Butler]

I am currently living in a condo with a roommate helping me pay my mortgage. I re-did the kitchen, floors (hardwood), bedrooms and finished the basement.

I am looking to use the equity I built in this condo as well as money I am currently saving to jump into real estate investing. My first move would be to use my VA loan (no money down) and either get a Duplex/Triplex, live in one of the units and rent out the rest for a year while invest in other properties. I would fix up my side while living there most likely - touch up the other sides before renting out.

I live in Worcester, MA and the real estate here is very expensive. For a Duplex I feel I have to get no more than a 250k property to break even while living there (been looking around and hard to find). A Triplex would cash flow more, but it would be a big stretch (Maybe future rent would help me get one) and I feel be better long term.

Should I start with a duplex and have not much cash flow if any or try to stretch into a triplex? Any areas around worcester that people are currently investing in that has been working well and a little cheaper?