shnoobles said:..A road bike would be nice, but I was worried about the roads getting too rough around here.
The thing you need to think about is whether you're looking to buy a vehicle, or a piece of sports equipment. A "purebred" road bike is pretty much the latter, excellent at its intended purpose but somewhat lacking in versatility.
It also require quite a lot from its rider in terms of conditioning and dedication for there to be a happy marriage. Riding on poor roads can definitely cause pinch flats and rim damage if a pothole catch you unawares. But the rest of the bike should be able to take most of it unless you run into something stationary.
Not all road bikes are created equal though, the subset of road bikes known as touring bikes can take fenders, racks and fairly wide tires, which make them a decent compromise between performance and utility value.
Next step is to look for cyclocross bikes(CX) or perhaps a bike built around something called a "winter training frame". These tends to take wider tires/fenders, while retaining a more racy geometry.
Over here, performance oriented commuters tends to favor CX bikes with disc brakes for winter riding. Fit a set of studded tires and you're all set for all-out effort under almost all conditions.
shnoobles said:...Would it be silly to get bullhorn / drop handlebars for a hybrid bike?
Well, sort of. There's a difference in fit between flat bar components and drop bar components, and (most) bullhorns will be considered part of the drop bar family.
Switching from flat to drop will require replacing far more parts than merely the bars.
It's doable, no doubt about that, and a search will throw up several threads of what's required to pull it off.
But as you haven't bought the bike yet it makes immensely more sense to get a bike in the configuration you think you want to start with.
Better then to fit a Trekking bar(part of the flat bar family) to a hybrid for a change of hand positions, or a shallow drop bar to a drop bar bike.
Another option is to fit drop bar ends to a flat bar. Not good for extended riding but gives you a hunched over position for occasional use.
shnoobles said:...Would having the vertical grips effect the riding position too much?
It's not as much about the verticality as it is about the reach and posture it requires. If you're fit enough to be comfortable in that position there's no issue.
shnoobles said:The generator hub looks awesome too, I'll look into grabbing one of those!
Battery operated lights are still the main choice for high performance applications, but a hub generator + a decent diode light will win hands-down from an utility riding standpoint.