Starting out, FHA or commercial loan?

[Haley M.]

Newbie here! My husband and I live in Boston. We currently own two properties - a condo in a good area of the city, and a home in CT that we rent to family that just about breaks even. We have rented out our condo for a few years in the past, but we're currently living in it again. So we have some experience, but not a whole lot. That said, we're looking to get started in real-estate investing, specifically buy and hold multi-family properties. Number one priority is cashflow. I'm looking at areas in Massachusetts that are more affordable than Boston but still have decent city access. 

We're debating about how to get started, however - is it better to get our feet wet with a few 2-4 family properties, or jump right into what we really want, which is larger buildings with more units (6+). Assuming we have the money to make the deal, is it possible to get a commercial loan without much experience in this area? Is it a mistake to start large? 

Any advice is appreciated, thanks in advance!