1. By design, the iPods are meant to automatically synch with one iTunes library, i.e.: one computing device. However, you can manually manage files on your iPod across multiple devices by:

Diplaying the iPod preferences.
Clicking the Manually manage music button.

Then you can move files from any iTunes client to the iPod. And yes, iTunes is a pain in the next for any non-basic functionality.

Posted at 1:50PM on Oct 15th 2006 by Kevin C. Tofel

2. I thought this was resolved with iTunes 7?

Posted at 2:13PM on Oct 15th 2006 by Joseph Scott

3. Ditto what Kevin said. Before I started using the laptop as the only machine, I turned my settings to "manually manage", which basically allows you to override the default iTunes settings.

Interestingly, it still did an automatic synch with the IPod when I plugged it in on the "main machine", but on the other machine I was able to just add the podcasts and music that I wanted.

iTunes has to be some of the most counter-intuitive software I've ever used, but I have yet to see any music/media management software that makes a lot of sense.

DnW

Posted at 2:20PM on Oct 15th 2006 by Drumsnwhistles

4. I'd recommend XPlay -

http://www.mediafour.com/products/xplay/

I use it when traveling, and it works great. I've been told that if you:

1) make sure your iTunes is set to manual (rather than auto) synch

and

2) It's formatted for Windows (rather than Mac)

you can do what you want w/o third party software. Can't say myself; I haven't tried. I use XPlay though, and like it a lot.

Posted at 2:22PM on Oct 15th 2006 by James Robertson

5. You should be able to do this without much hassle by having iTunes 7 installed on both computers. Are they both PCs? Macs? A mixture?

Posted at 2:37PM on Oct 15th 2006 by Andru Edwards

6. There's two solutions to this:

1) If you move your entire iTunes library folder from one machine to another, both will recognize and update the iPod as if it were its own. Obviously, this could create some management/backup issues (what if you import new music to one machine and not the other?), and there's all sorts of ways to overcome those. I personally do this on my machines so I can do exactly what you're trying - update my podcasts while on the go with my laptop, while I restrict importing/buying new music to my desktop in order to keep the real meat of my library organized.

2) With iTunes 7, you have very fine-grained control over what iTunes can update. They separated out music/movies/podcasts, etc. into separate management tabs for the iPod, so you could simply turn off podcast syncing on your desktop and simply leave it for your iPod, if that fits into your workflow better.

Ultimately, I recommend option 1 and simply setting a couple of rules for which machine you use to import your real music and movies.

Posted at 2:42PM on Oct 15th 2006 by David Chartier

7. ITunes drives me nuts (typing this on GNU/Linux, need I say more?). A while back I bought an iRiver 2GB flash player just to run with, but I found the convenience of simple USB HD transfer so much more to my liking that I find myself hardly using the 20GB iPod anymore. I've resolved to replace it with an HD player with similar (lack of) interface.

Posted at 3:17PM on Oct 15th 2006 by Yikes

8. I agree. That's why I rarely use my iPod any more for podcasts. (if at all now actually). My partner is constantly frustrated with it too. (and I say "see?!" ;) )

I met Scott from iTunes at the PPME and he was prepared to listen to some ideas on how iTunes could work better by not changing the way people already work and expect things to work.

But that was after the dust settled after I said 'iTunes sucks!' ;) - they mean well. I just wish they would participate more, then realise what users need.

It's more than brushed metal interfaces, thats fer sure ;)

Posted at 3:18PM on Oct 15th 2006 by Kosso

9. Just user third party software. Sorry I have lost links

Posted at 3:51PM on Oct 15th 2006 by Borzoi

10. It's funny, the people I've seen who simply say "iTunes sucks!" are the ones who have very simplistic organizational ideas, usually the same people who just want to drag files onto a player.

For these people, the natural way of re-ordering tracks is a matter of changing the prefix, 01, 02, 03, to create an alphabetical order within a directory.

While that works for 20-30 songs and podcasts, when you have a multi-thousand song/video/audiobook/podcast library, you really need a sophisticated, indexed database which makes them accessible. That's essentially what iTunes is: a database for media.

But what really gets me is how my 15 year old niece HAS ABSOLUTELY NO PROBLEM with any of this stuff, has smart playlists coming out of her ears and half a billion Harry Potter podcasts syncing to multiple iPods...

...and yet guys who use Linux are flummoxed and resort to "iTunes sucks!" explanations.

Maybe the problem is the girl doesn't think in a CLI world...

Posted at 6:51PM on Oct 15th 2006 by Reg

11. I use two macs and manually sync both as my library lives elsewhere based on size. I do however have it set to auto-download podcasts on both... works fine.

Posted at 6:56PM on Oct 15th 2006 by Jonathan Greene

12. I don't have any problems with iTunes, How many computers can you really put your music on, I mean isn't one enough, if you have to just stream it on your local LAN to other computer using itunes share, one hard drive is enough.

Posted at 8:58PM on Oct 15th 2006 by scott

13. i have been using iTunes on two machines for a few years now, no problems to report. But you do have to think things through on how you organize the iTune libraries, and see this http://www.engadget.com/2005/03/03/two-computers-two-itunes-libraries-no-problem/

Posted at 11:37PM on Oct 15th 2006 by vanni

14. I think Jason's problem comes with the computer+player bundle. It's ok when you have one computer and one player but when you have more of each it gets complicated. I think the real solution is a stand-alone player. Something like Mylo (haven't tried it) that have built-in wifi and can download songs without the need for a "base station".

Looking forward to a stand-alone wifi-enabled iPod... (Then I'll just use my Mac to backup the iPod).

Posted at 2:24AM on Oct 16th 2006 by Panayotis Vryonis

15. Yikes++ USB mass storage is the solution. I don't want DRM, smart playlists, auto-syncing. I just want to get my tracks on and off my player anywhere.[1]

Winamp 5.3 now does iPod sync. Try that.

iTunes is a bloated, overbearing, irritating, broken pile of junk worthy of Microsoft. But that's just my opinion. ;-)

[1]Oh for an iPod Killer(tm) that stops trying to play the game and is just optimised for Rockbox. With a replacable battery and upgradable hard disk.

Posted at 5:47AM on Oct 16th 2006 by Julian Bond

16. My brother is one of those "iTunes sucks" guys. He is convinced that the killer feature for MP3 players will be the ability to exist without a computer - rip CDs directly from a stereo CD player. Which is patently absurd.

The most frustrating limitations of iPod/iTunes stem from the iTunes Music store and it's obligations to record labels. If record labels weren't so thick headed about copyright protection and "fair use", Apple would not need to restrict use so much.

(Incidentally, I used a Virgin Megastore gift certificate at the Boston store, which is having a going out of business sale - all CDs 30% off. I picked up a Paul Simon CD originally released in 1972, and at 30% off it was still close to $15. And they probably blame the store closing on "piracy".)

Posted at 11:33AM on Oct 16th 2006 by Ryan Biggs

17. What about syncing an iPod on two machines when one is a PC and the other is a Mac? Is this possible without overwriting the firmware on the iPod itself?

Posted at 1:03PM on Oct 16th 2006 by Anthony Baker

18. Aside from manual management (what a drag, I know-- oops, that's a pun), if you want to keep the 2 iTunes libraries in sync (and that'll mean the iPod will sync whatever you want when you plug it in), go with Martian's little app that syncs 2 folders or iTunes (and playlists!). martian.com

Posted at 4:12PM on Oct 16th 2006 by Victor Agreda Jr

19. Winamp + ML_Ipod

http://www.winamp.com
http://www.mlipod.com/

You'll need to uninstall Winamp's built in ipod interface, but I think ML Ipod will do that for you.

I uninstalled Itunes after this.

Posted at 6:57PM on Oct 16th 2006 by Rizwan

20. Heard the last Gillmor Gang and all the comments about splitting up the show, and how that causes problems if iTunes is used as the podcatcher, etc., etc.

I'm surprised no one doesn't just get the parts of the Gang, string them together in to one show, and post it somewhere. It will cut the thing down by some 20 to 25 minutes after all the ads are gone :)

Posted at 5:37AM on Oct 17th 2006 by Diego