Boston - Has the ship sailed?

[David Lewis]

Hi Everyone,

Dave L. here! First ever post on Bigger Pockets. For context - I'm 35, own and live in a condo, unmarried, no kids.

My question to this forum - Boston is the third most expensive real estate market in the country behind San Francisco and NY. By the way, when I reference "Boston" I also include surrounding towns like Everett, Malden, Somerville, Medford, Cambridge, Watertown, etc. 

I'm having a hard time finding multi family where I'd even come close to breaking even. As a result I've sort of giving up on the dream. 

Thoughts/advice? Should I be thinking about this differently?