Rarely.. maybe once every month or so. I am like Tim and consider iTunes nearly incomprehensible and maybe even a virus. Admittedly, I know just enough about iTunes to be dangerous, as the following gripe list will no doubt attest.
But:
1) how do you handle multiple users on a PC with different libraries and different user accounts? What? iTunes is not meant to be used in a multi-user account environment?
2) how do you move the files on your iDevice to the computer after losing a HD (without using 3rd party software?) Oh? iTunes is crippled and won't let you do that?
3) do you really know what files you need to completely back up iTunes including playlists, etc.? (yes, I think I do... now)
4) how about using another computer to backup your iDevice(s).. we are allowed to connect to 5 computers, right? What? It says synced to another computer and wants to replace all the data on the iDevice with what's on that particular computer? I don't think so!
5) iTunes wants to backup your device. Do you have any control over where that backup is stored? No? Well that's great, I have a 60GB main drive (C:\) and a 300 GB data drive (D:\) and it wants to backup a 64GB iDevice to my C:\ drive? That ain't gonna fly. (ok, it's the kids' computer and they have two 64GB iTouches.)
6) when updating apps, I have to change over to whatever user ID got the original app and homeshared it with me. Really? Sheesh.
7) I do not want iTunes backing up to my C:\ (OS and program) drive. It is an 80GB SSD. I want to tell iTunes where to put the backup. Afterall, I have a 320GB data drive, a 2TB data drive, and a 1.5TB external drive with plenty of room. What? I can't do that? (see #5... already been there and done that)
8) I never really have any confidence that I know what iTunes is doing when I'm transferring purchases or syncing... or selecting options within iTunes. I hold my nose, close my eyes, and click the button hoping I'm not going to take out the entire eastern seaboard power grid.
9) argh. iTunes. Crippleware.
Please tell me my gripes #1-7 listed above are inaccurate perceptions of iTunes and are easily dealt with.
Sorry. Had to vent a bit.
OTOH, I am encouraged to learn that update OTA may be coming! Or is someone just playing a cruel joke on me?
