He's right, it's the American Way. Bigger, Better, More Expensive. I guess it's the same reason some guy needs a Lexus to drive 6 miles to work and back, or why do people who don't know the meaning of "Depth of Field" buy a digital SLR to shoot family snapshots. When you think about it most people could get by with a Toyota Corolla and a Canon "Point and Shoot".
But back to your question. I'm with you. I bought a Trek 1200c when I started riding. It's a great bike for me and I don't plan on buying another, ever. It suites my needs just fine. I also bought an inexpensive Gary Fisher, same story, good enough.
I'm pretty sure your Cypress is exactly right for the kind of riding you enjoy, so why change except to look better. Heck seeing as you don't do many hills, new lighter wheels may even be unjustified.
Now of course if I was 28 with a great body and trying to impress the chicks that's a whole nother story.