Glad to find someone in MA! I have no idea where I'm going yet, as I'm really just getting started after 16 years since boy scouts. I am waiting for temps to get up to where I won't die if I screw something up. Not dying is #1 on my list, but being comfortable is right up there, and avoiding issues with raccoons/mice and bears makes that task a lot easier. I am thinking this paint can idea would weigh about 12 ounces and be hangable. It's a lot cheaper than an ursack, and if I hate it I can always upgrade. But I can probably be talked out of it.
I'm thinking of starting with the Metacomet-Monadnock trail, though a section of the AT is tempting as well. I'd like to hike the White mountains, but only when I'm virtually sure I won't get snowed on. I expect to be safe (not comfortable, but alive) to around 15-20F, which I hear is a reasonable expectation in the warmer months. I don't intend to go anywhere until I expect overnight temps to be above 40F.
Also, I'm looking for hiking buddies. I have two family members interested but one is encumbered by a newborn and the other is probably limited to short outings (overnights.) My wife is not outdoorsy, so it's either solo or find a buddy/group to join.