Now that email, contacts, and calendar are taken care of, it's time for my music. I have 3 iPods (shuffle, nano, and 60GB 5G), and I already have an extensive library in iTunes on Windows. I want to transfer them to my Macbook without loosing any meta data like ratings and playcounts. There are various options in doing this. I don't want to be hassled by editing iTunes library database files manually, so I opted for the backup method. iTunes now has the ability to backup your library, albeit only to optical media. I haven't backed up my library ever anyway, so I prepared a couple DVD blanks and started the process. iTunes automatically divided my library and spanned them to whatever media I put in (mix of dual-layer and single layer DVD blanks). Pretty straight forward, although I wish iTunes can just backup my library into an external hard-drive, which will be much faster than waiting for the DVDs to burn. If you choose to backup everything, iTunes will back EVERYTHING, including all videos and podcasts, so make sure you have plenty of DVD blanks.
I was planning to have the iTunes library sitting on my networked storage, but later found out that syncing the library to multiple computers will be a great hassle. Local hard drive it is then. Restoring them is pretty straight forward too. I insert one of the restore DVD to my Macbook with iTunes opened, and iTunes automatically asked if I want to restore the music. After it finished with 1 disc, it will eject the disc and ask for another. At this point, you can cancel if you want to continue later, which I find to be great. iTunes seems to see any backup disc as an individual backup, so restoring your library partly is not a problem. Basically you can insert any of the backup disc in any order anytime you want, and iTunes will just restore that disc. However, when after I restore my last disc, iTunes still asked for the next disc, which I think can confuse some people (just cancel it and you'll be fine).
After restoration, I find couple things missing, namely the "last played" meta tag and my playlists. Those are missing. Bummer. I have setup playlists to rotate my songs based on the "last played" tag. For the playlists, I went back to my Windows PC, and start exporting my playlists 1 by 1 (oh I wish Apply can just include playlists in the backup). A slight hassle having to import them 1 by 1 to my Macbook. Also, I find playlists that are dependent on other playlists, will screw up. On my Macbook, those playlist seem to not be able to find the other playlists that they are dependent to, even though they are there. So I have to re-linked them 1 by 1. Another thing missed is even though all my podcasts are backed up, iTunes lost track on which podcasts I have listened to, so all podcasts came up as new. Subscription is also lost, so I have to re-subscribe all my podcasts.
OK, library is set. Now syncing my iPods. I know that Macs can read and write on PC-formatted iPods (not the other way around though). However, on my iPod setting screen in iTunes, I saw a warning saying that only Mac formatted iPods can be updated (firmware) via iTunes on a Mac! Another bummer! Since this is a switching plan, I took the dive and restore my iPods and have them formatted for the Mac (restoring iPods on Macs will automatically make them Mac-formatted).
I find iTunes on my Macbook is super smooth, especially when viewing cover flow. Viewing cover flow on Windows is very laggy, while it is silky smooth on my Macbook. I guess all that hassle gotta worth something. :)
So, not a smooth and hassle-free experience. Couple points in regards to iTunes:
1. If you set iTunes to backup your whole library, it will backup everything. For those that have massive library, this means tons of DVD dual-layer blanks, and slow burning process.
2. Backup doesn't backup playlists, "Last played" meta tag, podcast status and subscription.
3. You can only update the firmware of a Mac-formatted iPod on a Mac. Exception is the shuffle, which doesn't get that note on the setting screen.
4. You can restore any backup disc anytime without having to sit there restoring all discs in order at once.
Wish list for Apple:
1. Make the backup program to backup playlists and complete metatags.
2. Allow backup to use external hard-drives.