Organizing tracks in playlists

I have a ton of audio books (not from iTunes download). when I put them on my iPod classic (80g) then go to play them they are all out of order. I have tried re-naming the track names with 01,02,03... (etc) in front of them, but they are still off. Is there a way to make it sort right?
Also on a similar note. is there a way to make podcasts play from the oldest entry to the newest one? instead of new to old?

I have tried some experiments on my computer at work.
I have found that if you copy the library, and re link it to the new copied folder (in the advanced preferences), it doesn't seem to do anything.
After doing this I restarted iTunes, selected a song and hit "show in finder" and it was the same local location it started in!
Then I learned about holding option down while you open iTunes lets you choose a library. I figured this might be what I was looking for. I chose the new external iTunes folder aaand..... nothing; when I reveal a song in the Finder, it still shows me they are in the original location.
Then I added an extra step. I went to File>Library>Organize Library and checked "Consolidate files" which says it puts copies of media files used by iTunes in the iTunes Media folder. That sounds pretty good; if I've already moved those files there iTunes will surely see them in the new location and make the connection without needing to copy any files.... Not the case. iTunes literally added a duplicate to every single mp3 in my Library (really glad I didn't try this on my real library! what a mess!)
My next idea is doing this same process, but I'll direct iTunes to an empty folder on the external drive. Hopefully when I "Consolidate files" it will do it's copying process and work fine.
I much would prefer copying the files myself, however, for a couple of reasons. One is that I've already done the 18 hour file transfer using Carbon Copy Cloner. The other reason is that OSX is notorious with copying large amounts of files; almost every time I copy a large amount of data, OSX gets upset by some minor problem or a file that it doesn't like and it quits the whole process. I guess I'll go through these steps and let iTunes copy the data itself, and if that doesn't work I'll go to the genius bar.
Basically a lot of work and stress for moving a simple folder.

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