I have a Surly Cross Check and a Bianchi Volpe, each set up differently (handlebars, gearing, fenders/no fenders). I bought each on CL for less than 50% of their new retail price. Both had significant upgrades and were in 9+/10 condition. But I cruise CL weekly and bought each within a couple days of their appearance on CL. Still, after my initial set-up changes, each cost $500-650. Given that I ride almost daily year round and I dropped a car when I started utility biking, I have absolutely no qualms about spending the money. I recouped the money in the first year just by not owning the second car. And each rides wonderfully, so I would be hard-pressed to think I would be as comfortable or satisfied on cheaper rides if such rides meant more maintenance or lower performance. I already ride more than the fair-weather, recreational cyclists at work, and their bikes are in that $1500+ all carbon fiber, disc brakes, racing wheels range of the spectrum. I think my cost-to-performance ratio is optimized to the level that suits me.