Trying to sync podcasts in a certain order to iPod color

Howdy-
I have downloaded several podcasts to iTunes.
With automatic syncing, these copy to my iPod OK. I can access them in the Podcasts section of my iPod. But they are in reverse order (I wish to start listening to the oldest podcast & move "forward" in time, to listen to old radio serials in order).
So, I created a playlist in iTunes with the podcasts in my preferred order. But this playlist dies not auto-sync to my iPod playlists. I need to turn off the auto sync option in iTunes & then manually drag the playlist to the iPod for the new playlist to appear. But, if I then revert iTunes to the automatic sync option, the new playlist is removed from my iPod.
A search has turned up 1 option1 that doesn't work for me: If my iPod's On-The-Go playlist showed in iTunes, I could drag podcasts into it, but the OTG playlist does not appear in iTunes, though it is indeed on my iPod (however, it has never worked--if I push & hold the center button while playing a song, it doesn't add it to the OTG playlist).
Using an iPod Color 20GB.
Using a Win XP laptop w/ iTunes 9.0.1.8.
Thank you,
-Jason

Order them by track number 1 of 16, 2 of 16, etc. Rip an album and see how they are done by iTunes for you. By track number is how. Hmmm.....to be clear, as it appears you think calling it 01- Dance makes it track 01 (it doesn't):
In the info box for the track is a track X of Y set of boxes. There is where you enter both numbers. Note the "of" number is always the same if that's not too obvious....You can reorder a store-bought CD as well if you want, just change the number before the of.
Also post Windows questions in the iTunes for Windows forums. Although I doubt the cure is any different there.

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