With most anything I can think of (cycling, programming, building your own PC, photography, ..) there's two ways you can tell if someone is really good at it: either his equipment is brand-new, perfect and shiny, or his stuff is shoddy as hell and looks like it'll break down at any second. Here's some examples.
Cycling is the obvious example. There's people who always have to have the most perfect bike. The one that's 0.01kg lighter than every other bike. It must always be shiny and perfect, and the proper clothes must be worn while riding it. These clothes are of course also lighter than regular clothes. When it comes to cycling, I tend more towards the shoddy side though, and I take pride in that. My bicycle is heavy by any standard. It's dirty as hell, and despite having a lot of parts replaced recently, there's still plenty of bits that are held together by tie wraps and duct tape. I don't wear a racing outfit because 1. it would look silly on my fat belly and 2. it wouldn't match the bike. But I'm very happy with the way things are, and I wouldn't want to swap my old bike for a new one. Not until the frame snaps in two, anyway.
When it comes to programming though, I feel a bit different. When it comes to my own code, I'd rather have it in a state of shiny perfection from the get-go. But when I have to maintain code from others I'm quite happy with crappy code, because I can then start improving on it. It's no fun if it's already perfect from the start, unless you're the one who made it perfect in the first place. If I had to analogize that to bicycles, it's no fun to buy a brand new bicycle that's already in a perfect state, but it's ok to get a shoddy one and start fixing it up until it's as good as new. Strangely enough, I'd rather have the brand new bike.
Other examples: a camera that is scratched to hell versus a brand-new one with protective film and cover everywhere, a Macbook Pro versus a PC that is held together by duct-tape (but overclocked and blindingly fast), and so on. On most of these examples I tend to the shoddy side of things, although I certainly don't mind shiny either. How about you?