I cross the border all the time with bikes in the car. Just take off any tags that make it look new and drive through. It would help if you have a bag of dirty cycling clothes in the car too!!!
As for the insurance you need a velo vignette. They can be got from places like Denner or the post office, they are pretty cheap and last until may of the year after purchase. i.e. If you buy one now it is valid until May 2009.