Sharp makes a neat range of IR rangefinders such as this one
http://www.robotshop.ca/sharp-gp2d12...-sensor-1.html You can order them in a range of sensitivities and so long as you are looking at something that is not particularly reflective (such as diamond plate) in the IR spectrum then you can usually get a good distance reading by simply reading an analog input.
In fact, now that you mention that, we should probably strap a couple of the ones we have on the shelf on to the front of the robot so we can do some rangefinding on trailers when we come in to dump on them.
As for the idler wheels, you are allowed to use omni wheels... VEX robotics makes some nice little ones (and an encoder to match up with them) and you could always use the AM omnis... they would run parallel to your drive train at all times.
Can't help you with the round belting question, though... this is our first time using it, too. So far all we've learned is that the 3/16" hollow core falls apart really, really easily, while the 1/4" hollow, 3/6" solid and 1/4" solid are darn near indestructable at their joints.
Jason