A couple of iTunes/iPod questions ~or~ How do I make my 2 computers and 2 iPods love each other?

1) In sync mode, you can't play music off of the iPod. You have to have the iPod hooked up in Manual mode in order to browse its music library and play it while docked to the computer. (I think what you want to do is probably keep the iPod synched with the computer at home, but manually associated with the computer at work. Then you can listen to its contents using your work machine. I think you can do that.) 2) No. If you add content when the iPod is synched to one computer, then sync it to a different computer that doesn't have the content already, the new content will be erased from the iPod. It will not be copied "up" from the iPod to the computer.* Basically, the iPod is not designed to be synched to multiple computers. It works best when you only sync it to one computer, and then use it manually with any other computers that you might attach it to. Since it is intentionally broken designed to disallow true bidirectional synchronization, you will run into issues trying to use it to keep two computers in sync. (Basically, you are not supposed to use an iPod to keep two computers in sync. Which sucks.) This is probably the most glaring, totally artificial limitation of the iPod/iTunes combo, and I think you can lay it squarely at the feet of the copyright lobby and Apple's pandering to them. * Possible exception: I think new versions of iTunes will copy purchased DRMed music from the iTunes Music store from your iPod to a computer during a sync operation ... but this is the ONLY iPod-to-computer movement (of tracks; metadata moves freely) that iTunes allows. Normal tracks, including Podcasts, can only go in one direction, and that's from the computer to the iPod. To go the other way, you need special tools.

You can install Rockbox or iPodLinux on the iPod Nano, and use something other than iTunes on the computer, and then you won't be subjected to this kind of demeaning copyright-nanny "fair use who?" software restrictions. There are many benefits and a few downsides to replacing your iPod's firmware, as the two options' wikis will explain. Afaik, the new iPod Classic hasn't been broken into yet, but that will probably change soon if it hasn't already. Next time you want a new player, I hope you will express your dissatisfaction with Apple for creating these barriers by buying a cheaper better player from someone else. The iPod hasn't been the best portable music player for years now, and most of the competing devices allow you to read and write the music using Finder or any other program (except iTunes, which of course does not let you put music on removable devices other than iPods). A question for you: When you purchased the iPod Classic, were you unaware of the restrictions around the iTunes library syncing? Or, did you just assume you'd need to figure out how to circumvent it somehow?

Since the latest iTunes sw clearly HAS code to sync files bidirectionally (after filtering "files" down to "iTunes Store-purchased files"), can a hack to remove that filter be on the horizon? Just saying.

To add a plank to my own rickety bridge... since even DRM-free songs from the iTunes store work this new bidirectional way, do you suppose the iTunes software just checks for the "store-bought" meta-information when deciding whether or not to sync a given file? If so, um... even easier opportunity for someone with a smidge more time than I have this week. Whoever reads this and gets so-inspired, drop me an e-mail via my profile, pls.

(except iTunes, which of course does not let you put music on removable devices other than iPods). That's not true. 1. With my new Classic in Sync mode, I can't play music off of it in iTunes at work (everything's greyed out), and with it in Manual mode, it doesn't automatically sync. Am I forced to add every track I add to my home library to my iPod manually? WWWWHHHHHYYY??? You shouldn't have to add them all manually -- just right-click on the iPod and choose Sync. It'll update your iPod with new songs.

Thanks. bonaldi, I'll test this when I get home. It's odd that it would still sync if it's in Manual mode, but I noticed it still says it's syncing when you plug it in. I guess i'll have to use my own workarounds for the podcast issue, I was hoping there was a way to do it "officially." rokusan makes a good point though.

@bonaldi "That's not true." Are you sure? I haven't used iTunes in a while, but googling for non-iPod iTunes just now indicated that it still cannot access other players without resorting to unsupported hacks or 3rd party software. do you suppose the iTunes software just checks for the "store-bought" meta-information when deciding whether or not to sync a given file? Probably, yes. But doesn't it also check if the computer doing the syncing is the one allowed to? And even if you were to "fix" (break) this mechanism to your liking, if you publicize it don't you think Apple will just "break" (fix) it again in an update? Can't you see that Apple's interests and your interests are no longer compatible? (I switched to Linux about a year ago, after a more than a decade of using, supporting, and recommending Macs, and it is working out very well here.)

finite: http://docs.info.apple.com/article.html?artnum=93548 -- and I don't think this list is exhaustive, either. I agree that Apple's interests are no longer ours, tho.

I stand corrected about iTunes being unable to access any non-Apple devices. It can apparently now access a handful of models made by Creative, SonicBlue, and Nike, and one by Nakamichi. But, from the looks of that list, it still can't access most of the portable players out there, or any of the ones I'd recommend buying (iriver, Archos, SanDisk, lots of others). Which is strange, because almost all of them use the same totally standard USB Mass Storage protocol. If iTunes still can't put music on a generic USB thumb drive, then it still isn't compatible with most models of music player. (The iPod also functions as a USB Mass Storage drive, eg the way it shows up in Finder, but songs copied to it that way cannot be played by the iPod's firmware.)