Choice in how I manage iTunes on iPhone and two computers?

Question

OK - so first off, because as I read the history this appears to be sensitive, I HAVE read a considerable amount of previous threads on this. It's hard to believe that at this point (Apr 2010) there is still no third-party software for this? Apple must have made it virtually impossible!
At any rate, here's my situation:
(1) I have two computers - one iMac which holds my primary iTunes (computer 1), one new MacBook (computer 2), and one iPhone 3Gs.
(2) I also have MobileMe which syncs everything just fine in terms of contacts, calendar, etc.
(3) My iTunes and Music folder for my iMac IS located on an external drive off of my iMac (computer 1) and not on the actual hard drive.
Again, to stipulate, I understand:
(1) iPhone is set up to sync to only ONE computer
(2) I can authorize up to 5 computers. (My issue with this is that I have considerable amounts of my own music imported that will not appear as the "authorized" music. And, I do this regularly so I don't want to have to keep duplicating the MP3 import - I'll quickly become out of sync or lose track of them.)
(3) Trying to sync from iPhone to new iTunes library will wipe out iPhone or vice versa
And, I have read this thread on the code changes that can be made:
http://discussions.apple.com/thread.jspa?messageID=10972003
Plus I read this thread on iTunes library being an external drive:
http://discussions.apple.com/thread.jspa?messageID=11148807
SO, now that I've made my case for being informed, I'm asking for your help in how to make my choice to structure my situation.
My basic desire is to have the same library on all three places - I don't need different things in different places. Same thing. And, I pretty much have access to all three devices all the time (one is not physically located somewhere else). I would, however, like to be able to purchase on any of the three and then have it added to the library for all three - and I think that's where I run into my problem.
Option 1? My iTunes library and entire music library IS located on an External Drive off of Computer 1. So, technically, could I just set my MacBook (computer 2) iTunes to pull from that library? Then, any new purchases would go into that same library, accessible by both? The risk here, I think, is that I cannot try to sync to the MacBook when I am NOT on my home network with access to that external drive? In fact, on my MacBook, should I set it up this way iTunes will be "missing" it's library completely? Second risk - how stable is this plan? Am I likely to corrupt/kill/worse my iTunes library from this set up? (Caveat: It is backed up nightly on a second external)
Option 2? Do the code changes posted in the articles linked in this thread:
http://discussions.apple.com/thread.jspa?messageID=10972003
But my iPhone is not jailbroken, nor do I intend it to be - does that matter? And, how stable is this? Honestly, I don't like the idea of monkeying with iTunes code.
Option 3? Copy my iTunes library from Computer 1 and then set up as iTunes library on Computer 2. Designate one computer / iTunes as the one I both buy music on and sync with my iPhone - then can I manually transfer music added to my iPhone into the Computer 2 iTunes (hit cancel when it says it will delete the library if it's synced. go into iPhone and choose songs to manually transfer?) Not sure this is possible...
Option 4? ? ? Is there something else here I've missed?
I hope this all makes sense - I've spent a lot of time reading about the options and think I understand each, I'm just wondering your advice in terms of which is the best solution.
Thanks!
Message was edited by: akcorcoran

Answer 1

My basic desire is to have the same library on all three places - I don't need different things in different places. Same thing. And, I pretty much have access to all three devices all the time (one is not physically located somewhere else). I would, however, like to be able to purchase on any of the three and then have it added to the library for all three - and I think that's where I run into my problem.
Short answer:
I'd suggest a variation of your option 3, but use "home sharing" to greatly simplify the process of keeping them in sync. If you really need to sync the iPod with different machines, then maybe your option 2 is best, but I share some of your apprehension about that solution.
Long answer:
I have a similar issue: three desktop machines, one PC in my office, one Mac in my wife's office, and one Mac connected to the audio system in our living room. I have an iPhone, and so does my wife. I also roam the house with my Macbook. We keep all three desktop machines synchronized in terms of the basic collection of music, and my wife and I synchronize our individual iPod devices to our respective desktop machines.
My solution was to (despite the many complaints about this feature) employ "home sharing". Basically, not only do we share our libraries, but we've also enable home sharing on all three machines, all registered using the same Apple ID. We further more have set the "home sharing" options so purchases are automatically purchased.
It's wonderful. If I buy something at the iTunes Store on my PC, we've configured "home sharing" so it magically shows up on the other machines, with no intervention on my part, just as do purchases that my wife makes on her Mac. And on those occasions where I rip a new CD, while "home sharing" won't magically transfer it for me, it does have feature that you can (a) look at another computer's library, showing only those tracks that don't exist on the current machine; and (b) you can drag and drop music, right in iTunes, from one machine to another. Thus, in comparison to the nightmare of my pre v9.0 manually synchronizing of libraries, "home sharing" has made this much easier.
And in this set-up, my wife and I can each maintain our separate playlists for determining what's sync'ed to our respective iPods. Yes, playlists and ratings are not synced between the three PCs, but it makes it possible for us to take advantage of this to make our own playlists. (This feature is probably less of an issue for you than for us, but it's very useful for us.)
The only problem I see is that it sounds like you want to sync your iPhone with multiple computers, whereas I've explicitly decided I want to sync with a single computer.
I'll answer some of your questions below, but this is a configuration that we use, doesn't involve working around any iTunes features (like the manual manipulation of the iTunes library ID) or problems with file contention. We also have a built in backup of our iTunes library, so if one machine dies, at least all of the media files themselves are safe. (Having said that, I do backups, as well, so I've got a double redundancy.)
Option 1? My iTunes library and entire music library IS located on an External Drive off of Computer 1. So, technically, could I just set my MacBook (computer 2) iTunes to pull from that library? Then, any new purchases would go into that same library, accessible by both?
That might work, but you'd have to think about, in addition to your media files (the mp3 and other audio and video files), whether you'll put the library database file itself (the separate file that keeps track of what media files are available to iTunes, where they are located, the playlists, rankings, play counts, etc.) on that shared drive, too. If just the media files are there, then I suspect that might work, but anytime you add or remove content, you'd have to update the other library, at I think it would be more cumbersome than the "home sharing" approach.
If you decide you want to keep the iTunes library on this shared drive, too, that might eliminate the need for the syncing process, but you might run into trouble if you're not careful about ensuring that the references to that external drive are identical on the two machines. Also, if you try running iTunes at the same time on the two machines, I can imagine that you might have file contention issues on the library database itself.
Bottom line, might work, but seems that you would have the choice between a cumbersome solution and a fragile solution.
Option 2? Do the code changes posted in the articles linked in this thread ... But my iPhone is not jailbroken, nor do I intend it to be - does that matter? And, how stable is this? Honestly, I don't like the idea of monkeying with iTunes code.
You don't need to jailbreak your phone to do this. And I suspect that it's reasonable robust solution as I've seen CNET training videos that advocated for precisely this solution.
This seems like an acceptable work-around if you're trying to sync phones in disparate locations (home and office). But it seems unnecessary if the machines are on the same network, and like anything where you're trying to tweak software behind-the-scenes, I'd worry about it being susceptible to it breaking on new updates to iTunes. Apple isn't going to ensure that some hack like this won't be broken in future releases. I'd be shocked if they tested this scenario in future releases.
Option 3? Copy my iTunes library from Computer 1 and then set up as iTunes library on Computer 2. Designate one computer / iTunes as the one I both buy music on and sync with my iPhone - then can I manually transfer music added to my iPhone into the Computer 2 iTunes (hit cancel when it says it will delete the library if it's synced. go into iPhone and choose songs to manually transfer?) Not sure this is possible...
As I described, I'd suggest a permutation of this option, where you use "home sharing" to keep the machines in sync. I'm not sure if I follow your thought process on "hit cancel when it says delete library...", though. Were you thinking of using the iPhone to sync the machines? If you have a home network, that's not necessary. Or are you saying that it's important to sync the iPhone with multiple computers for some reason that I'm not understanding.
By the way, if the issue is that you want to be able to manage your iPhone from either machine, what I do is I've designated one of my computers as my "iphone sync" computer. When I want to manage this (e.g. download apps for my iPhone, etc.) when I'm not at that machine, I "remote" into that machine from wherever I happen to be sitting. (I use Mac "screen sharing" to access my wife's Mac from my Macbook, I use Microsoft "Remote Desktop" for Mac when I want to access my PC from my Macbook, and I use a free VNC client when I want to manage my Macbook or my wife's Mac from my desktop PC.) Yes, when I sync I have to plug in the iPhone into the cradle in my office, but because I can access that desktop PC from wherever I happen to be, I find that to be a manageable solution (e.g., I'll update apps and podcasts on my desktop my Macbook in the basement, and then walk up to my office and just drop my iPhone into the cradle when I want to sync). I'd love remote syncing, but Apple ain't there yet.
Message was edited by: Rob Ryan