I'm jealous! Cycling in Europe sounds amazing :) The US has pockets of good bike trails here and there, but in general we are way too car-oriented.
> The difference is night and day. I wish I did it sooner.
Especially if you're not so hardcore and only occasionally cycle! The difference between a $100 and $1000 bike is HUGE. $1000 to $5000? Not so much.
IMO the sweet spot is getting a lightly-used bike at a professionally managed bike swap sale where professionals and mechanics are actually looking at the bikes being sold, not just rusty things off Craigslist. Often times some rich person will buy way more bike than they need, don't end up using it much, and then letting it go for 3-4x less just to free up space. But to a beginner-intermediate cyclist they are still amazing machines.
There's soooooooo much technology that goes into them, everything from the drivetrain to the materials to the aerodynamics to the brakes... it can make a huge huge difference in comfort, especially over long distance.
Fit is another big thing: adjusting the bike with small tweaks (saddle, handlebars, stems, etc.) can change it from "painful" to "dreamy" depending on ergonomics.
But all in all, a good bike is probably the single best investment I've ever made. Cheaper and way more fun than paying for either a gym membership or a doctor.