Following up...
Indeed, setting up a folder as a 'handheld' device and syncing appeared to work fine. I would have had to do a little more fine-tuning with regards to the directory structure to deal with multi-disc sets and my podcasts, but it looks like it would have been a perfectly acceptable solution.
However, I ended up using some built-in iTunes functionality. Because I'm going to be solely on my Macintosh for the next several weeks (away from the HTPC and the media server), I was able to use the "Consolidate Library..." function in iTunes to copy all of my music onto my external drive. If you try this, remember to change the default location of your iTunes music library to your destination folder, make sure that 'Copy files to Music Library' is selected, then use the 'Consolidate Library' command.
I did take the precaution of backing up my Mac's iTunes library BEFORE consolidating.... Everything went great! I can use my new, consolidated library while on the road, then switch back to my original library once I'm back in range of my media server.
Thanks for the suggestions!
Brad