This shit is svelte!
iTunes, however, is a miserable bitch goddess. I don't know if it's just because I'm a Windows guy trying to use an Apple product or what, but I find iTunes very difficult to use. I just find the interface doesn't have the options I think it should, and if they are there, they're not in the places where I expect to find them. I consider myself a fairly experienced computer user, so in general, if I can't easily figure out your application, most of the time, your application is stupid. I'm willing to forgo that statement for some pieces of software that are inately complex, but not for a music manager like iTunes.
First of all, If you want to keep your sanity, UNCHECK the checkbox that says, "Keep iTunes Music folder organized". That thing scares the hell out of me. If your MP3s are not properly tagged with ID3 tags, then who knows what the hell is going to happen. iTunes (and the iPod) work almost entirely on these tags. They are what both pieces of technology use to display when browsing your library of music, and while playing a particular selection. The only way to reasonably keep track of things, is to have all your MP3s tagged properly. I have found that a good program to do this with is called (logically) Tag & Rename. It lets you generate ID3 tags from the filename of an MP3, and vice versa. It lets you do in a more tolerable way, what iTunes would have fucked up from the start.
Ok, so that's the first problem out of the way, but don't worry, there are lots more. Number two on my list has to be the automatic update feature of iTunes. This is supposed to keep your iTunes library synchronized with what's on your iPod. Now, even I'll agree, this sounds pretty good in practice. You can have a complete copy of your music in a nice portable form that you can listen to on the road, while you're walking, attending funerals, etc. It kind of breaks down when your music collection is like mine, and far, far larger than the 30 gigs afforded you by the (what now seems) tiny iPod hard drive.
Luckily, there is another option that would seem to be exactly what the doctor ordered: Automatically update selected playlists only. This would seem to say to me that whatever is in the selected playlists would be kept synchronized with the corresponding tracks in my iTunes library, but everything else on my iPod would be left alone for me to manage manually. Unfortunately, this was not the case, and I ended up having to re-copy about 10 gigs of music to my iPod after iTunes mercilessly deleted it. Therefore, the only option left for me to use was the third and last: Manually manage songs and playlists. I don't revel in doing anything manually...I mean, come on, that's what computers are for. I shouldn't be subjected to anything *gasp* manual. But I didn't really care...With 30 gigs of space, I didn't figure I'd be changing the music so much anyway. Except for podcasts. New ones download every day. How the fuck am I going to deal with that?
Whew! iTunes to the rescue! Somebody thought enough to stick a podcast tab in the configuration options. That should take care of everything...right? Well, as it turns out, not so much. I don't know how many of you know this, but I am subscribed to (as of this writing) 51 podcasts. (It's not as bad as you think: They're not all 1 hour long like Spine Radio, and they don't all release new episodes as frequently as once a week.)
Even though I'm sure iTunes would be more than capable of handling the multitude of subscriptions, there was no easy way to move these subscriptions from my other (and current) podcast downloader into iTunes. And even if there was, I wouldn't really want to use iTunes for it. Because I subscribe to so many shows, the sheer size of all the downloads can grow quite quickly, so I would rather my podcasts download onto my server machine at home, the one with the terabyte of disk space, and not my laptop. I'll go into my podcast receiving set-up at some point, but not right now.
Anyway, since I basically couldn't use iTunes as my podcast downloader, I had to figure out a way to somehow automatically get podcasts that were being downloaded onto, and shared from, my server machine onto my iPod. As it turns out, that's not trivial. Unlike Windows Media Player, iTunes does not have the option to monitor a directory in your filesystem, and automatically add any files to its library that it doesn't have yet. When I used a Windows Mobile device to listen to podcasts, this is exactly what I did. New podcasts would get picked up by Media Player, and a smart playlist would sync them to my device. With no way to do the same in iTunes, I'm left with a problem. But, hey, I'm a software developer, and this problem is starting to look a little bit like a nail.
Non developer types may want to skip to the end of the marked section. Anyone who's interested, or suffering from insomnia, feel free read all the gory details.
After a little bit of googling, I found out that iTunes has a COM interface.. Perfect. I fired up my development environment and went to work. It turns out that iTunes interfaces aren't so much a programming interface as they are the COM representation of the iTunes program itself. If there was a menu item or button you could click on the GUI, there was a method on a COM object you could call do do the same thing.
However, since I could accomplish what I wanted to do via the GUI, I could also do it via the interfaces. With a pretty shallow learning curve, I whipped up a small command line app that just scanned my podcast share for anything that was newer than the last time it had run, and added those items to the iTunes library. It would then do its best to synchronize any new podcasts over to the iPod (if it was connected), and remove any old ones that I had already listened to. It works pretty well, and it serves the purpose; even if I do still have a breakpoint to make sure it doesn't delete anything its not supposed to.
I know people are saying that there are other applications out there (like EphPod or Anapod Explorer) that can replace iTunes for getting music on your iPod, and while this is true, these other applications did one of two things:
1. screwed up my iPod's internal database, and rendered my iPod incompatible with iTunes, or
2. couldn't do (or be configured to do) what I wanted them to do, in which case they were really no better than iTunes.
The third major problem with the iPod/iTunes one-two punch to the sack was that once your music is on the pod, there is no supported way to get it off and back onto your computer. There are some applications that can help you with that problem, though. They include, but are not limited to the afore-mentioned EphPod and Anapod Explorer, as well as SharePod, and YamiPod. From what I've read, older versions of the iPod just stored your music in a hidden folder on the iPod itself, that was clearly visible when you turned on the "hard drive" option. In the iPod with video, however, the files are placed seemingly randomly into folders named F00 to F49, and the filenames are munged into random 4-letter strings, i.e., MMSJ.mp3. The programs I mentioned will read the appropriate information from the iTunesDB file on the iPod and rename the files according to artist, album, etc., when you copy the files off.
So, after all that, if you still want an iPod, I think you'll be happy. The iPod itself is a great device, and I highly recommend it. iTunes can go suck an egg.