I'm having major issues and I'm fed up!

Question

I got a nano in July, and I use it ONLY to listen to audio book. This is an issue in itself. If a book isn't available at the itunes store (I get books from the library) I can not get info on it, and the only way to listen to it is through recently added since the music library loads them as track 1 track 1 track 1 track 2 track 2 (etc.) Can you imagine how annoying this is??
Anyway, my newest issue is that somehow my recently added setting on my ipod disappeared. So I look under my ipod music setting and it's been unticked! When I try to update it, it will not go back onto my ipod. So all my tracks are shuffled! This is even more majorly annoying!! Then every time I try to do any changes to my ipod, the itunes program starts telling me that there is not enough space, I have too many playlists! Wait, just before I did the update I had 50 mgs free. Now I have nothing? So I unchecked all 248 tracks of my 14 disc audio book. Nothing changes, still tells me there is no space available. Ah, but now I've finally got recently added back on my ipod! Unfortunately, there's not a single track on my ipod. But the itunes program keeps telling me there's no free space...do you get the picture here? Now I can't get anything to upload onto the darn ipod.
I'm at a loss as to what I should do next (besides throwing it out the window into my pool, which is what I feel like doing). The ipod is not audio book friendly at all, oh, unless you purchase the book in the itunes store! What a rip, I wish the sales person had told me what a pain it would be to listen to my beloved books, I never would have bought the stupid thing.
Needless to say, after writing this book, any help would be greatly appreciated. If this ipod is caput I will not be replacing it. I'll by a generic mp3 player and download books from the library (oh yea, apple format is not supported by the library, if I'd known that I also would not have bought the ipod).
Nano 1.3 itunes 7 Windows XP

Answer 1

Well, no one seems to have any answers or ideas for me, I'll update what I've been able to accomplish.
I reloaded all 14 disks in the time frame of watching Lord of the Rings on Fri. nite.
Funny thing is, the first disk pulled the info from the online store! Hooray!
Wait-then all the next 13 could find no information online...what the heck is up with that? So I MANUALLY assign each disk a new track # to co-inside with each disk, spent about 2 hours doing that.
But still, itunes tells me my playlist is too large, there's not enough space on the ipod. so I unchecked 1 1/2 disks (I'd listen to 1/2 of disk 1 previously) and voila! there's my ipod full of my book. Finally. But what a lot of bother just to keep things in order!