HT1386 I can no longer sync my books to my iPod touch.

Question

Okay someone help me out, PLEASE!
My daughter and I bought new e-books and wanted to put them on our iPods to read with iBooks. First I tried with my daughter's. I added her books to her iTunes account. Her settings are set to sync all books, rather than selected books. I clicked "apply" then clicked "sync". Then I got an error message saying it could not add the 4 files (the four new books) because they could not be found. I double-checked and they were still showing up in her iTunes library where I'd put them but kept saying they could not be found when I went to sync. I also kept getting the message "cannot connect to iTunes store" which was odd but my daughter's had lots of issues with her iTunes before so before I pulled out anymore of my hair I decided to switch over to my account and put my new books on my iPod.
Umm yeah that wasn't happening either. I have mine set up to only sync selected items. I added all my new books into my iTunes. I opened up my iPod settings and went into the book section, found the new books I wanted to add, checked them all and clicked "apply" then "sync". I never got an error message, however I also didn't see the little writing during the sync that would say "adding [book title]" either. So I checked my iBooks account and sure enough they aren't in there. I tried several dozen more times, I even tried switching my settings to sync ALL the books in my iTunes and it would not add any new books at all. And before it's suggested YES, I had the room/space on my iPod for the files (same with my daughter).
This happend to me once before and I got totally frustrated and annoyed and ended up deleting every single book out of my iTunes, as well as deleting my iBooks app altogether. Then I readded iBooks and re-added a few books at a time to my iTunes account and synced and it worked fine. The next time I had a few books to add I held my breath sure it wouldn't work but it did. And the next few times was fine. Then today this happened again! I really don't want to have to take all my books off again (as I'm in the middle of reading one) and delete the app, etc. so I really hope someone can suggest something else. I'm about to just say screw it and sell my iPod and get a kindle or a kobo or something.

Answer 1

Well, I can see a potential problem with that, although you must have made it work before.
I had a set up on a Windows computer like that, but the iTunes accounts couldn't communicate or share content.  We consolidated, after much fuss, to one Library, one location. 
This may be why your daughter has problems connecting to the iTunes store.  The "server" is serving 2 accounts.
I am sure it is why the books didn't sync and can't be found on her iTunes account.  If you look on her iTunes on the computer, are the book titles pale gray?  is there an ! point on them?   This means that while the computer knows they were there, they can't connect with the actual content.   After all they can't be in two places at once.   iTunes can sometimes offer to "rebuild the path" to lost files, I don't know it that would work here.
As for why they come and go from your device, I can only guess it is because they are not iTunes purchases.  Just like my PDFs, iTunes tolerates them, but really doesn't know what they are, or what to do with them, so it does nothing. (unless you make it!)  Not that iTunes treated the iBooks I did get from iTunes any better.
As I posted above, the only way I could get it to work was to delete stuff, which seemed to shock iBooks into syncing the books and PDFs.  Maybe, finish the book you are reading, delete all then add new books?  (Sorry,it's all I got)
If you are going to share content, one iTunes Library, but separate Apple IDs would work better.  But that is up to you (I'm also a parent, I get it)  I share with my 2 sons.
You mentioned a Kindle.  I have one.  Never use it, but it is an older one.  The paperwhite seems like a good idea.  It is absolutely impossible to transfer PDFs to the kindle in a print size big enough to read unless it's
24 pt type going in.  Didn't work for me, might work for you.