Getting Started in Boston - What Should I Know? Will This Work?

[Colin Alsheimer]

Hey everyone - looking to get started investing in the Boston area (Boston and surrounding towns, that is - i.e. Cambridge, Somerville, Medford, Arlington, etc). My wife and I are currently renting and are looking to buy our first house.

We've decided to make that purchase be a small multi-family unit - ideally 3 or 4 units, and live in one while renting out the rest. In an ideal world the rent cash flows each month and turns a small profit while covering expenses and the mortgage. What I'm expecting, however, is that we break even and it just opens up or own cash flow from no longer having to pay rent / mortgage from our own pockets. 

We're ideally looking for properties in the $400-$600k range that need anywhere from $25k-$100k in reno work, and using an FHA 203k loan to fund.

Once that's all done, the plan would be to use the increased cash flow to save enough for a down payment on another property, and keep buying new properties in this way.

Thoughts? Anything I'm not thinking about? Any insights into the Boston area market?