When I first started pulling pocket queries and stopped printing out cache pages, I used gpsbabel on my Mac laptop to load caches on to my Garmin Vista through the serial adapter and a USB-serial converter, and I used gpx2ipod to load caches into the Notes folder of my iPod in disk mode. Around the time I got the Garmin 60CSx, I began to experiment with MacCaching and CacheMate to load caches on to the 60 (USB!) and a Palm III (through its serial adapter and the USB converter) that I bought in 1999.
Two things became obvious very quickly: first, it took the Hotsync manager about TWENTY MINUTES to load a 500 cache .gpx-turned-.prc on to my Palm III (which I think may be made out of wood, I'm not sure). Second, MacCaching is just not happenin'. Its map utility plots the first five caches in the database and that's it. Useless.
So, back to gpsbabel and gpx2ipod. I am trying to address the map issue by investigating some Linux tools like gps-map that rickrich has developed for use with gpsbabel. Still working on it -- I had to install Xcode and MacPorts, and I think something may still be missing, or I've got something in the wrong directory. Work in progress.
gpx2ipod is also fluky. It puts Notes on the iPod at a blazing speed, but sometimes I'll get out to a cache and realize that the relevant cache file is missing. Also, sometimes it chooses the filename to be the GC number and other times the filename is the cache nickname. Maybe these are the same issue.
Until I get in the groove, I am printing screen shots of the geocaching.com Google maps interface and WRITING in the GC numbers near the icons. How lame is that?!