i had no end of trouble with my wifes itunes when she bought an Imac, she wanted her music off her old computer on to the new one, but as itunes seems to register your device to itunes and all your tracks to one device it won;t let you trnasfer them very easily. (her itunes was bigger than her device, and she only decided she wanted it after i had partially dismantled her old PC so was trying to pull it off the hard drive.
i don't like the layout, i don't like the format, i don;t like the way the software embeds itself so deep in your CPU.
i didn't used to like the fact that it only wrote music in apple format (this has now been changed) which meant you could only play stuff from itunes on apple devices.
Itunes and apple stuff is fine for people who have no interest in computers, but if you want to do anything outside the apple parameters its incredibly frustating stuff ti work with.
Erm.... no it isn't
If you do a fresh install then the default settings are to rip tracks into apples own format, which is actually very good compression and quality wise, certainly better than MP3 but anyway I currently have over 50,000 tracks on iTunes and have no problem when I reinstall windows on my PC something I do every few months to keep everything working well
If you set up iTunes correctly to manage your folders and music files it organises them, moves then wherever you want it to when you add them and if you use mp3tag then everything looks spot on too...
I think the problem is more 'user error' than Apple's software
I have my PC in the front room and I can control iTunes via my phone, tablet, one4all remote I can even sit in the bath and change the tracks on my speakers in there while the missus is watching Emmerdale
The most frustrating thing I have found is if you have a device, say an iPod with lots of music on and the PC packs up and it won't let you synch to the device but there is plenty of free software out there that lets you plug in the device and extract all the music from it just like it was a HD, I have done this many times for friends