I've been living in Randolph for years now and love it! There's so much history here, not just in Randolph but the whole region. I love being close to so many museums. In the summer, the city really comes alive and there are a lot of farmers markets and festivals you can enjoy.
Getting around the city isn't too hard. There are buses that can take you to the downtown area, plus the train can bring you up to Boston if you want to see a Sox game. For me, the best area of the city is down by the cinema. It's a fun part of the city to see and I love going to see all the newest movies.
Since Boston is so close, there are practically unlimited possibilities for work and school. There are a lot of young professionals and startup companies in the area, mostly in technology. If that's your area of expertise, you're in luck.