Originally Posted by solo
I faced a similar question about three years ago. I converted a 2001 Wahoo to a commuter (1.25in slicks, fenders, rack) and found it was great for the mostly flat terrain (some low hills) on my ride. As I built up strength, though, I found the low gearing was a big limitation. After I moved to an area that was more vertical than horizontal I decided to try a cyclocross with a 52/39 crank and a nine speed 11/32 cassette. It's been great and has made the commute faster and more fun.
I can't offer advice on the expense or technicalities of the crank change, but it sounds like a lot of fiddling to arrive at a sorta/kinda road bike. Have you test ridden any road bikes to get the feel of a larger chainring and nine speed drive train?