Originally Posted by Madmick
I have a Calibre library with over 14,000 titles right now (about 8,000+ are MOBI and most of the rest are PDF), and I've meticulously edited all of these titles so that the Titles and Authors are perfect.
When my brother asked me to import a few thousand of these into his iPad...
You need to get out more. I read a lot. I seriously doubt I've read more than 3000 books in my lifetime. I might make it to 5000 by the end. I might not.
In truth, your basic problem is you're trying to force these systems into doing a job that almost no one needs. The designers never anticipated that anyone would handle this sized library. I'm glad iTunes worked so well. That's Apple's good design skills and tight control over the hardware/software environment showing. Don't expect that in a diverse environment.