It's not just (or maybe even primarily) about money. As is indicated in the first part of the OP, changing things means changing things that a lot of people are fine with, affecting many businesses, causing a lot of disruption, etc.

I'd be fine with more walkable areas but it's not just about spending money.

IMO this is a question of ignorance. Most Americans simply don't understand that there are (far superior) alternatives to car-dependent suburbia. It's just not on their radar.

Hopefully channels like "Not Just Bikes" and our own social dissemination of the walk/bike/transit oriented urban development model will allow more Americans to understand what they're missing.

Once enough people in a given urban area realize what they could have, perhaps the political will to improve will materialize.

I don't much care for suburbs and like cities only in moderation. I prefer the country within striking distance of a large city. I'm perfectly aware of what an urban environment is like--I've lived in both Cambridge and NYC--and while there are things I like about it (I'm staying in one this week) it's not something I want full-time.

Seeing as those are both American cities, it's not surprising you don't like it. Even our best cities are pretty disappointing when compared to what Europe and Asia have to offer.