*Btw your cartoon on your blog is good. If that's your original creation you might consider developing it out.
You basically get the extremes of everything in Boston at a much lower price.
Possible downsides are long, snowy winters, and far fewer jobs.
You should write for the Lonely Planet :-)
Working remote can definitely be isolating anywhere, but I think if I were going to go back to it I'd prefer a midsize city to either rural or dense urban settings. Rural settings are obvious just small, and that's made harder by being isolated while you work. But huge cities tend to feel anonymous - if you're not actively engaging and meeting people it's easy to get forgotten or even miss out on finding out about things you'd like to see and do. It may just be a function of my tastes and hobbies, but somewhere Springfield-sized makes it a bit easier to find a stable group of people outside work to spend time with.
More broadly, there's a lot to be said for college towns and non-huge cities relying on safe anchors like 'meds and eds' or corporate research. Boulder's probably too big and pricy these days, but Northampton, Rochester NY, Flagstaff, Ithaca, and the Research Triangle are all inviting. Heck, even Fargo ND was shockingly inviting last time I came through - I'd rather live there than Cleveland.
The food scene in Northampton is great by the standards of rural MA. There are only 2-3 restaurants there that are any good at all.
Which obviously isn't what people normally mean by "food scene", my brain just approximated the topic as "well, it's better than all those rural places without any good grocery stores".
But Providence is actually a nice exception; lots of events, good food and activities, several colleges, but pretty cheap housing and not terribly dense or gridlocked.
I wish I could draw those cartoons. I work with a freelance cartoonist named Loraine Yow (https://www.lolo-ology.com/). I wrote a blog post about how the process works: https://mtlynch.io/how-to-hire-a-cartoonist/