Maybe not exactly the direction this was meant to go, but my mind started churning when I read the responses earlier on my break at work, and I've had some time to consider the topic from my own perspective...
I started cycling in earnest about a decade ago, at the age of 19. At first it was out of necessity because I move home from college without a car, but it quickly led to being a hobby and then a passion. My first road bike was my 1979 Raleigh Super Course 12, and since then I've had nearly twenty road bicycles in all, a handful of which I never got on the road before selling, and most of which were vintage. I love riding them, and my most recent acquisitions are among the oldest and most unique. The 1951 New Hudson has pre-war geometry and all sorts of in-house BSA fittings with pre-war designs, and the bicycle is very rugged but generally rather lackluster in performance. On the Carlton Continental I broke the Simplex Durel Grand-Prix 3-speed shifter housing on one of my first outings and had to have that brazed back together, and now I worry about it every time I shift. These two bicycles are rather precious and riding them takes me back to an era of cycling that I find fascinating...
Still, the issues with performance and reliability do not pass without angst on my part. Lately I've had my longest riding season in several years and plan to stay in the saddle as often as possible. I've owned and ridden three brand new bicycles, all both with MSRPs of over $2,000. All of these bikes were sold rather quickly due to typical financial constraints of a 20-something with an odd work season, much more than my actually wanting to part with them. They were absolutely better bicycles than any of my vintage rides - better power transfer (especially during acceleration and climbing), faster and more diverse shifting capabilities, and better braking performance. A couple of them were even comfortable to ride for long distances.
However, even the 853 Reynolds Raleigh Gran Vitesse frame had a particularly hollow feeling to it. The performance was amazing, but there was nothing spirited about the ride quality. Nor did I like to look at it very much - I think both it and my 2003 Raleigh Team were lovely looking as far as modern bikes go, but they did nothing for me compared to a vintage lugged steel frame with slender rubes and polished components. I even missed the down tube shifters!
I'm trying to figure out where my middle ground lies. I realize now that I'm in a position where I could sell just a couple of my nicer vintage bikes to afford a new, reliable bicycle that has that lugged frame and some shiny Campagnolo group set, and am wondering seriously if I should do so.
Maybe I don't always feel like toughing it out, but I do always love to ride. Sometimes I think that having a powerful and dependable modern steed might be better for my riding than the old heroic bike is for my ego. Tough choices...
-Gregory