Investing/House-Hacking in expensive areas

[Jake Freeman]

I have leisurely studied real estate for a few years without ever getting too deep since I was full-time in school. I recently found BP and learned there are more than 1-2 ways to get into real estate. I have been really focusing on wholesaling and multi-families but I think the best way to get some experience is to house-hack. I am very fond of the idea of having others pay the mortgage or just a small payment myself while learning the responsibilities of being a landlord. 

Since finishing school I do have loans, so my main goal for now is to create enough cash flow one day to completely cover the payments each month. I currently live just south of Boston, MA at home trying to save as much as I can which isn't easy with loans. I have realized a lot of 2-4 units around me are 1. Really expensive 2. Very old. I am not picky in any means on where I live, but I just want to find something that is livable and not crazy expensive. I know the FHA loan is the way to go but I just wanted to also get any advice, tips or tricks on investing and house-hacking in areas like this.