The more I use iTunes, the more I miss WinAmp.
I'm on my second iPod, which I purchased to increase my portable capacity. My library is significant (I passed 500 CDs years ago), and laptops are not practical to store so many music files, so I've relocated my music to a NAS. Relocating those files means adjusting the defaults for iTunes so it can find the data.
This is very manageable - for each specific version of iTunes. Upgrading, though, produces all sorts of chaos.
For some reason, every time I upgrade iTunes, the new installation loses all the marker information, including album artwork. It isn't readily apparent until I start downloading new data: new purchases, new imported CDs, new podcasts. At that point, the upgraded software begins storing these new files in the application's default location, and loses track of the NAS-housed data.
I can reconfigure the software to find the files on the NAS with little difficulty. But peripheral data, specifically the album art, is a far different story. It's not clear how iTunes stores this data, but every upgrade has lost something, and the latest one (to v8.1) lost about half my album covers. There's no apparent pattern, and whether the data was found through iTunes and the store or uploaded manually seems to make no difference. Worse, some albums downloaded from iTunes itself lose artwork, again with no apparent explanation. This is true from (and here one gets a glimpse of my library) a-ha through Yes, and varies without predictability: some Asia albums retained their artwork and some did not, and artists as current as Amber and as esoteric as the Wien Volksoper lost artwork while others did not. Some - including some very popular artists - had the correct artwork actually replaced by iTunes with completely unrelated material: iTunes really ought to know the difference between Wilson Phillips and Nathan Phillips, but at least with this upgrade did not.
I've always respected Apple as a desktop platform, and the iPod and iPhone seem like highly effective gadgets as well. But this regular data loss, however insignificant to the actual music files, is disturbing. A software publisher such as Apple should be able to manage upgrades without data loss of any kind. Further, regardless of the current availability of a product through iTunes, items purchased through Apple should be able to be maintained without having to go through these gyrations with each software update.
I've spent a good portion of the morning on Amazon and Discogs digging up replacement artwork - much of it either already uploaded to iTunes or obtained from Apple with the particular albums. Resync has only been partially successful: despite specifying artwork for an entire album, in at least two instances only some of the tracks display properly.
I've researched this on Apple's Website and found nothing. Apparently Apple doesn't see a need to provide support for functionality it clearly considers as secondary (despite having made considerable noise when the 4G iPod was released about this particular function). I'm still looking in outside sources for more information.
It's true that other music file management applications have similar features. And it's true that iTunes wasn't tailored for the audiophile, and some of its controls are less than ideal. But it is a useful tool for managing an iPod, and once a version is configured properly it's pretty stable. But upgrading iTunes presents far more difficulty than others - and here I'm thinking of WinAmp in particular - whose functions, while not completely iPod-compatible, were at least carried over in whole from version to version and required very little in the way of reconstruction of the database to resume normal operations.
If anyone from Apple is reading this, I would say that anyone familiar with databases would be most unhappy with iTunes in this respect - and that the lack of thought put into the product regarding management of secondary data and file location specification calls into question Apple's other database applications.
Excuse me while I go dig up some more graphics for the other items still without pretty pictures.