Try looking at www.syncmyride.com
and see if their forums have this resolution posted. I think mine play in alphabetical order (Artist Name) when random is disabled.
Don- for playlists on the iPod, on the Sync screen, in one of the menu items (sorry, memory failing) you can see all the playlists and select 1 to play from.
I use both a flash, and iPod. I keep the iPod in the console out of sight, all winter. No probs. (if you are wondering how, search for "Mystic Second USB port" here and there is a great thread on how to get at the second USB port, what to use, and how to route a wire to the console or glove box to keep the iPod/iTouch/external drive hidden).