Rookie in Boston, MA

[Erica S.]

Hi all,

My fiancé and I currently live (rent) in the North End neighborhood of Boston, and while we love the location and convenience, we're both sick of forking over 1/3 of our income each month in rent. I've been doing research over the past 6 or so months and know for sure I want our first property to be an investment. I've found a lot of great info on biggerpockets so I figured I would ask you all directly to please help me! :)

Boston and the neighboring towns seems to be one of those areas that (from what I've seen) simply never meets the 1 or 2% rules. So we're ultimately looking for something that will cut down our monthly costs (either through lower cost of living or supplemental / rental income).

Option 1: Purchase two or three family owner-occupied home. By doing owner-occupied we'd get to take advantage of the lower down payment which is great. But in this scenario in towns like Quincy (or first choice) or Dorchester/Eastie etc., my model shows us not cash-flowing at all (we'd still need to put in ~$1000 per month, which is much better than what we pay in rent currently, but still). 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? 

Option 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. Positive here is that the condos in this market are (for the most part) all updated and would bring in higher rent whenever we move out, versus the multi-families on the market which would likely need to be updated (at very least cosmetically) before we could get the same rent prices.

Since this turned into a long-winded and very specific question/prompt, any insight/advice you all have specific to the Boston/South Shore markets would be much appreciated!

Erica