track numbering in itunes, won't respect track numbering order

I'd suggest using the convention 01, 02, 03 for track numbers - perhaps adding that at the start of the name of the track and sorting by name rather than album to keep the order. Hope that works for you.

I am not sure if this will help you but it works for me with CD tracks.
Is the Track # column displayed in your library. If not you can bring it into view by checking "Track Number" in View options or right clicking in the row with Name, Artist,Album etc.
You can then sort on this field by clicking on track #.

Keep in mind that iTunes and the iPod do not care about filenames. For instance, Chapters 1, 2, and 3 of an audiobook could have the filenames "apple.mp3," "pear.mp3," "grapefruit.mp3" for all that it matters. The filename is irrelevant. What matters is the entry in the Track Number box.

Here's how you can apply the correct track numbers to all the files that make up an audiobook. Make a playlist, and fill it with the files. First thing to do is make sure they all have exactly the same book (album) title so when you play that "album" you will hear the whole book. An easy way to apply the same album title is to select all the files (Ctrl-A), press Ctrl-I, and fill in the Album Title box.

Next, arrange the tracks in order manually. If you can't seem to drag the files up or down the list, be sure you have the very first column of the window highlighted, the column with no name. After the files are in order, select the first one, and press Ctrl-I. On the Info tab, typing "1" in the first Track Number box. Click the Next button at the bottom. Type "2." Keep clicking Next and typing the next number until all the tracks in the book have numbers.

Now iTunes will keep the tracks in order, and more importantly the iPod will play back the tracks in order.

Again, don't worry about renaming any of the FILES; filenames don't matter.

Keep in mind that iTunes and the iPod do not care about filenames
Actually, yes they do. The filename is the song/track title which is the ID3 tag info.

I am having the same problem.

When you number the songs on the iPod, there should be no other factor deciding in what order they play.

It's like this

1
2
3
4

Come on, apple.

You need the track number and total tracks (n of x) in all the tags.

Keep in mind that iTunes and the iPod do not care
about filenames
Actually, yes they do. The filename is the song/track
title which is the ID3 tag info.

Not to split hairs, but I think the ID3 tag is the ID3 tag. The filename does not matter. When there's no tag found, iTunes resorts to using the filename, but that doesn't mean the filename has the ability to change existing ID3 info. The file can be "grapefruit.mp3" and the ID3 tag can be, "Elvis - Ain't Nothing But a Hound Dog." Renaming the file will have no effect on the ID3.

XP Home, Pentium 4, 3.6 gHz, 1GB ram, 160 hd Windows XP 2nd gen iPod for Windows, 10GB

I think the ID3 tag is the ID3 tag
Correct.

but that doesn't mean the filename has the ability to change existing ID3 info.
Correct.

The file can be "grapefruit.mp3" and the ID3 tag can be, "Elvis - Ain't Nothing But a Hound Dog." Renaming the file will have no effect on the ID3.
But changing the ID3 tag CAN have an effect on the filename if iTunes prefs is set.

Yes.
Don't rename the actual file.
In iTunes, right click on the first chapter, then select Info.
Keep the name, artist and album (book) what they should be.
Don't name it 001-Chapter 1.
Make it something like Chapter 1 - The Beast
The track # should 1 of 287.
You can select all the chapters and do this to edit the common info of all the tracks (Album, artist, total # of tracks, etc.)

Here is some good info on converting CDs to audiobooks.
Aldo on Audiobooks