Hi Erica,
I can relate, I'm 24 and was in a similar scenario just like yours. I've researched Boston and surrounding areas in and out, its near impossible to find something within 15-20 mins of Boston (thats not a tear down) that will cash flow within while you occupy the home. Here are some suggestions-
1. "So big question here is: long term, is it worth getting a multi-family that won't cash flow as owner occupied, but has the potential to do so once we're renting out all units?"
- Personally I would not buy a multi family around Boston at this point in time unless you would be converting into condos or found an off market DEAL. You need to treat a multi family like a business, if you aren't cash flowing why buy it? Anything in Boston thats on the market right now is extremely overpriced. If you are really set on looking for a 2-3 family, look in Chelsea. The Silver line extension is heading over there and prices have not skyrocketed yet, but they are on the rise.
2. "Purchase a (much-less-expensive-than-a-multi-family) condo in an up and coming area like Quincy, save a buttload on rent, use those savings as capital for our next real estate investment (or get a line of credit based on our equity in the condo), then rent the unit out when we move onto bigger and better things."
- If you want to get into the real estate game, buying a condo will only set you back. ( thats just my opinion) If you were to do this you would be losing out on using a FHA loan to your advantage.
Bottom line-
If I were you I would look for some multi families in Providence and DO YOUR RESEARCH. For example, I bought a 2 family for $170k last year with an FHA loan and put down only 3.5% up front. My expenses totaled $1,500 a month.I was bringing in $4,200 a month just off that home alone. (minus expenses) I put some sweat equity into this house ( along with $7,000 in materials) and I just received an offer last week of $250k. This would enable you to save up some money for a multi close to Boston while living in the North End.
If you want to get into the real estate game you have to make some sacrifices. I was living at home traveling back and forth to RI every weekend to make this multi family work. I now own 2 multi's in Providence and I just closed on a triple decker in Sommerville for a condo conversion.
-Patrick J. Gleason
Design Builders and Contractors inc.