I can’t speak much on the living situation other than I would look on Facebook. The one time I had lived with random roommates that’s where I found it. I won’t lie, it’ll likely be hard to find a low wage job and afford a place for both of you while having spending money to enjoy the city. You’ll likely have to look a bit outside (try Watertown, Everett, Brighton).

As for work. If you have any experience working with kids I strongly suggest looking for a town/city job working at a camp. You’ll meet a lot of people, you’ll be outside, get exercise, and really get acclimated to a natural sense of community. I ran a camp 6-7 years ago and pay was around 15-16 a hour for high schoolers without experience. I imagine it’s even higher now and given you’re 19 it opens you up for a higher position.