I just went totally paperless using a Garmin Legend C and Palm m105 And I absolutely hate having to go through multiple programs to massage data into different formats. Most efficient way I've found so far is to download the Pocket Query (.gpx format) and upload into GSAK. You need GSAK ($20, voluntary) on your PC and Cachemate ($8, required) on your Palm.
You can also export your Found List once a week and GSAK will update automatically. Write a easy filter for for "not found by me" and you are ready to export to both the Palm and the GPSr.
GSAK will then export all the info you need (including hints, previous 5 logs, description, waypoint name, size, difficulty, terrain, etc.) to your Palm. GSAK also can download the same set of waypoints directly with into your GPSr. No problems.
Then when you are caching you can log your find on the cache page in your Palm (includes space for Took, Left and TBs - but no comments - just add it to one of the three fields). I understand you can also automatically upload your logs ingo GeoCaching.com but haven't tried that yet.