If he doesn’t care if his finds get logged online, you could simply load a bunch of coordinates for caches into his gpsr and let him go to town. Just make sure the caches can be found with coordinates alone- i.e. puzzle caches & some others require additional information you can only find on the cache page.
Most really active geocachers upload cache pages onto a PDA, which does away with the need to print out cache pages altogether.
I routinely keep 700-800 cache pages in my PDA and the coordinates for them in my GPSr. This way, I can go all over the place and always have the data needed to hunt caches. I update the data weekly, to help ensure i’m not hunting caches that have been archived. Once you have a system down, the whole process only takes a couple of minutes.
.
