I wouldn't worry so much about walking but parking my car? Higher chance than most of Boston it may get broken into.

Native Michigander who now lives in Salem,+1 for Coffee Time!

+1 Mapparium! I enjoyed bringing out of town people here when I lived nearby

Check out Watertown, most of the area has super easy bus access to Harvard Sq/red line.

Logan Express (I take it out of Peabody, but there's other options depending on where you're coming from, like Woburn and Framingham I think) or parking at the Wonderland garage and taking the blue line the rest of the way.

Sounds like you haven't. Would a shithole state have cheese curds?

A lot of these 'shithole' states are so gerrymandered, it's hard to even say they are a democracy anymore. You can't blame people for not voting when decades of republicans have deliberately closed polling stations in 'democratic' areas, making wait times hours long, required ID at the polls that can be expensive or difficult to obtain, etc. It's not so black and white.

Maybe too fancy or too far, but I always enjoy Cliff House in Maine. I go when they're cheapest - usually February - and their cheapest is luckily the most I'd ever spend on a hotel. Took my mom there who has some mobility issues, it was nice to not have to go far for food/spa/nature.

I've never really seen the appeal of the south shore.