Maybe DeLorme's geocaching support will shake Garmin out of their complacency and actually push them to fix things like this.
Had contact with Garmin. Had updated the firmware to V2.98 beta (V3.01 beta is out right now, see Firmware page)
And started experimenting with GPX files. It still goes wrong when you download the file from Geocaching.com directly into the Oregon. Even with the latest version of the browser plugin. But when you download the GPX to your PC and copy it into the Oregon yourself all looks fine! Even the buttons Description and Hint work fine now and will take you to the corresponding section of the text. Little side effect... the hint is already decoded in de Oregon.
Paperless Geocaching with multiple waypoints is still on the wishlist. But we're getting somewhere now.