I'm a college student living in Boston, and I started using a bike instead of the T for basically all my travels about six months ago. I got a 2004 Trek 1000 for free from a graduating senior, and it's been a great bike after quite a bit of repair work, but I have a few problems with it:

- I'm currently running 23mm tires in order to accommodate fenders. It can take 28s, but I'd rather have fenders. Anyway, this leads to a pretty bumpy ride; a lot of the pavement on my daily (<2mi) commute is very, very rough. I have to choose between flat risk and bumpy rides, which is annoying.
- I'm not confident in my ability to maintain the rear derailleur very well once the roads get really salty. It's already a little funky, but I figure I'll probably wait until spring to replace it. I only use 4 (very occasionally 5) out of the 24 available speeds, and I never use the front derailleur.
- I'd like to have a chainguard so I don't have to roll up my pants to ride. I can't do that with a front derailleur, although strictly speaking this is fixable without a new bike.
- It has not been treated well by its previous owner, and a lot of the parts are past due for replacement. None of them were very high quality originally, anyway.

Given these issues, I'd like to get a new bike that mostly fixes them. My roommate got a Motobecane Fantom UNO from BikesDirect that he turned into a fixie with bullhorn bars, and he really likes it, but I don't think I'm ready to go that route (yet).

I'd like to get a bike that looks a lot like his, but with drop bars and a rear freewheel and IGH (let's say 8 speed). That bike in particular doesn't have wide enough rear spacing to accept an IGH, although Sheldon does have some information on widening that, since it's a steel frame. I've gotten really used to the geometry of my Trek 1000, and I really like it. I mostly ride on <4-5mi trips, with occasional "it's too nice to stay inside" longer rides. A couple questions:

- Is an IGH a good idea? What are pitfalls/things to watch out for?
- Where should I find a bike with wide enough rear spacing to accommodate the IGH? My total budget is probably around $5-600, and I don't really want to pay for derailleurs that I'll just remove.
- Am I totally insane?