let me actually try my best but put my dc cap on for this:
-the no happy hour thing sucks, it just does. but in exchange there are so many good craft brewers to explore, it almost makes up for it.
-fenway bars are the equivalent of k st bars or douchy georgetown/gw undergrads frequent, avoid avoid avoid
-you're going to give up so much square footage for the rent. I pay the same in rent here than I did in DC for like 2/3 the apt space. Most apartments are also super old, little closet space, lack of in unit laundry.
-invest in footwear and outerwear, I don't mean buy one good winter coat. buy all types of coats. get a light fall jacket, a light rainjacket, if you get a warm down coat you will also need a waterproof snow/winter coat, rainboots, snowboots, wool socks, layers layers layers
idk this is a lot harder than I thought it would be, but im happy to answer any qs!