"And as an adult, I haven’t spent as much time in Harvard Square."

That's basically the problem. (Not you, specifically) but people who don't live in a neighborhood, who don't visit, don't shop there. don't work there, don't spend money there, don't own property there, don't run a business there--they don't usually get a voice in how a neighborhood develops over time.

"Harvard Square isn’t what is used to be." It's like The Neverending Story. You have to go there. You have to participate. You have to be part of the story. Or else it gets consumed by the Nothing. (again, speaking in general terms--not trying to call you out)

This is the answer. Parking meters are not for all-day parking, and OP is abusing them. OP even admits that getting repeatedly fined for their behavior is cheaper than paying for legitimate parking and still complains that the fines are too high.

I ate there once in '95 when I first moved to Cambridgeport. I'm happy to celebrate their getting 40 years out of that location, but I'm also looking forward to what's next. I love that cities are constantly in flux. Visiting my rural childhood town, I find it depressing how recognizable everything is. So little happens, so few changes...

Central Square is becoming a victim of its own "success". Every block on Mass Ave is turning into fancy restaurant, dispensary, fancy gym, cocktail bar, bank branch, repeat. Can't imagine what commercial rents are like now.