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The problem with paid parking in the US is we need to supplement the perceived/actual scarcity with adequate alternatives. If parking is made paid because of demand, that is one thing, however if made as a deterrent to drive, that is another and alternatives should be thought about before plans for paid parking are made.

Who was paying for the parking before?

I'm the same way, if there's only paid parking, or a parking shortage, I just don't go there unless forced.

I definitely factor in the price of parking when deciding whether to shop at X vs Y location. There’s very little reason for me to go 3 miles into Boston to shop when I can go 3 miles in another direction and shop in a suburb with free and plentiful parking.

I don’t see the problem; I get what I need and the people in Boston presumably get what they need. If a shopkeeper wants to cater to traffic that comes by car, they presumably set up shop in a suburb (where rents are cheaper anyway).