My reality check was that none of this is expensive. That was a little freeing. I look back on bikes I thought were "expensive" and I would buy them in a second today. I am content with all my purchases. Some I move on because they don't thrill me to ride, but I've never felt I didn't get my money's worth even if I lost a few bucks. If I didn't buy a C&V bike, I would buy something new. I think the new All City steel bikes are great - good looks, good quality, good functionality. You will be in for about $2,000 for one. I have bought C&V team bikes for less and unique hand built custom C&V for a lot less. Like anything new, the second I ride that new All City or Trek or whatever out of the store, I have "lost" money. I could lose money, make money or break even on a C&V bike. Seems I am no worse off than if I bought a new bike. In the meantime, I get to ride someone's creation, someone's work of art. That is worth something to me.
Like others, I have refined what I buy over time. I have sold a lot of bikes that I bought early on. I'd have to think, but I'm not sure I own any from my first year of buying C&V as a collection. My interests are still relatively broad, but I have passed on bikes that I would have purchased three years ago.