Earlier quoted context omitted.
One of the hardest parts about buying a home, apart from all the stuff that isnt fun about buying a home, is finding somewhere that is walkable to... anything. I've rented my whole life and spent my entire adult life in cities. The idea of having to get in the car to get milk or something from the corner store, or have to drive to ANY restaurant, or not have some type of walking/running path within a few blocks of my…
Town around 50000 is a good bet then. If you can work remotely, find a college town and live outside the center, about a mile. You can bike to anything, take the bus, or just walk. I did this. I have 100 restaurants, too many bars to count, music and theatre (three!) and festivals and arts within trivial distances. No car needed.
Unfortunately, there are relatively few places to live inside the dense part of town. The city is overly-zealous about maintaining historic districts and you'd better believe people get all up in arms about "changing the character of the neighborhood" every time a new development is proposed, even in non-historic and totally dilapidated areas. I've seen literally hundreds of millions of dollars worth of new housing and commercial projects be cancelled or indefinitely postponed due to this attitude just in the last 10 years.
While the city has a lot of potential, it's population has stagnated since the 1970s and the surrounding area has become a massive suburban sprawl. Many of the buildings downtown have been replaced with parking lots. Traffic is generally terrible, and the bus system has low coverage and poor frequencies.
Around 100 years ago, Portland was a thriving metropolis with electric trolleys going to every imaginable destination. All of those trolleys are gone now and their tracks have either been removed or awkwardly paved over.
Portland was once a vibrant inter-city train hub with hourly connections to the rest of Maine. The two primary stations, Union Station, and Grand Trunk Terminal, have been torn down. The current train hub, "Portland Transportation Center" is much further from the city center to make room for a large parking lot. It is about a 40 minute walk from what is considered the downtown area. 20 minutes by bus if your schedule happens to line up.
It's pretty disappointing how much better it once was. I'm doubtful that it will ever be as good as it was back then, but still hopeful. There are plans to move the train station back to where Union Station was. New routes to Lewiston and Rockland have been studied (although would apparently cost hundreds of millions to repair the tracks). The state has recently subsidized certain interstate train and bus routes to make them very affordable. And generally I think a lot of problems could be immediately solved by straightening out bus routes and increasing frequency, as well as obviously removing a lot of building-size restrictions and parking minimums.