In terms of actual performance gain from a wheelset, I'm always amazed with how much money you need to spend for how little time-gain you get via wheels.

Compared to the low-end stock wheels that came on my intro-level road bike, $2000+ top-end deep-dish racing wheels (actually, a Zipp rear disc wheel alone will cost $2000 alone!) will probably shave off no more than 1-1.5 minutes per HOUR of racing that you're doing.


You will gain more than 1 minute per hour just by wearing a tighter shirt that doesn't flap as much, and there is data out there to suggest that just wearing booties over your shoes will shave off 45sec-1minute per hour (not sure I believe this, but the data from 2 studies were posted on Slowtwitch.com fairly recently.)


For me at least, there are only 3 reasons for me to upgrade my wheelset, and one of them does not even apply to me.
1) Heavy rider requiring a especially bombproof designed wheel to avoid breakage. (Not me.)
2) Someone willing to pay $$$$ for that extra minute per hour of racing. (Also not me, and I train with competitive roadies where speed is really, really important.)
3) BLING factor. <===== Probably the least mentioned, but most common factor for upgrading to deep-dish aero wheels.

I totally disagree that the wheelset is the best upgrade you can make on the bicycle. One could definitely argue that spending that $500-$1000 on a coach would be a far, far better investment. Or even taking the hours you'd have to work to earn that money and spending that time cycling would be a better investment in terms of performance.