First, you should be safe in continuing to use iTunes as your music organization library. You'll still be able to sync your playlists onto your Pre using one of the apps we detailed here. It's not guaranteed that direct iTunes sync will break in the future, since Palm might still be able to find some kind of workaround; but even if they don't, you have multiple ways of doing it yourself. If you want to be safe, you could just switch over to one of these other library management solutions now, and not have to worry about iTunes anymore. [Gizmodo]

The problem with downloading to iTunes 8.2 from 8.2.1 is that isn't quite as straightforward as replacing the iTunes app. You have to replace some other support files. The easier way is to use one of these four options. And, you have the freedom to update iTunes to any future version without worrying about whether or not it'll mess up Pre syncing.

1) doubleTwist, by DVD Jon. [Download]

doubleTwist lets you access your iTunes Library in that you can see all the music and playlists (even smart ones) you've already established. Once you connect your Pre in USB mode, all you have to do is drag playlists or individual songs over to the Pre to have it sync. There's no library view, as in you can't drill down into artists, so you should organize your songs into playlists you want to sync inside iTunes first.

The downside of this method is that there's no progress bar so you can't see how much of your sync is done. The syncing process also isn't foolproof, and froze on me mid-sync. But it does have the ability to import YouTube videos, which is kinda awesome. And, it doesn't support the actual playlist function on the Pre, so your songs are going to be in one big pile. (You can sift through Artists, Albums, and Genres, of course.)

Update: The Windows version has automatic playlist sync (screenshot here), and the Mac is getting it this fall. What I meant to say was, the playlist support doesn't work on the Pre side, not to be confused with the playlist support on the computer side. Jon of doubleTwist tells me that the Pre doesn't actually support playlists in non-iPod mode right now. Hopefully that'll come some time in the future now that the iTunes sync is becoming an issue. Thanks Jon!

Best all-around experience since this is a media-manager in itself

Doesn't support playlists, and lack of progress bar when syncing

2) Just dragging music over into the media folder

One feature of iTunes that not many people know about is its ability to just drag and drop songs from iTunes the app to any location. So if you open up iTunes to the playlist, select all the songs inside the playlist and drag it into the Pre's USB drive.

Drawback to this method is that it's still one-way sync (you can't uncheck or check a playlist to sync or de-sync easily), so you'll have to clean things up yourself after your sync. It has the same no-playlist support problem as doubleTwist

Easiest method

Bare bones: no playlist support, no song management

3) iTunes Sync on Windows [Download]

It's essentially a very simple version of doubleTwist, where you can select playlists one by one and sync them over to the Pre while it's in USB drive mode. This does have a progress meter, but it's Windows-only.

Progress meter is a plus

Windows-only

4) iTuneMyWalkman [Download]

Mac-only, but it creates a M3U playlist when you're syncing music.

There are other utilities, of course, but one of these four should be enough to get you started. If you have one that does something better than the ones here, feel free to share them in the comments.

Playlist support!

Mac-only

Update: Commenters are also recommending Mediamonkey, Missing Sync and Salling Media Sync. You can give those a try as well.

It's an extension of their other Missing Sync products that are already out for BlackBerry and Windows Mobile. It lets you grab contacts and calendar (great), as well as ringtones and podcasts, both of which were able to be synced before just with the USB disk mode. It costs $40, which is kinda high, but better than having to loop your contacts around into Google every time you want to do a sync. [Mark Space via Boy Genius]

Faster syncing with Mac and PC. Changes you make to contacts and calendars on your Mac (Address Book and iCal) or PC (Microsoft Outlook) are now automatically pushed up to the cloud every time you make an update. Likewise, changes you make on me.com, iPhone, or iPod touch are automatically pushed to your Mac or PC. As a result, your contacts and calendars update faster across all your devices. To take advantage of faster syncing, be sure you're running Mac OS X Leopard 10.5.6 (Mac) or MobileMe Control Panel 1.3 (Windows).

After a lousy launch in 2008, Apple decided to avoid associating the word "push" with Mobile Me until they could get synchronization between computers and mobile devices (iPhones, iPod touch) down to acceptable times. Looks like it's close enough now to bring the term back.

Another new feature, iDisk file sharing, has been around since the 13th. Improved iPhone notification and syncing and better web app performance round out the improvements.

Dear MobileMe member:

Over the past few months, we have been working hard to make MobileMe the best service it can be. Here is a summary of the improvements and performance enhancements that have recently been completed.
Easy file sharing. iDisk now makes it even easier to share files that are too big to email. Simply select a file in the iDisk web app and click the Share File button to generate an email with a download link. You can also optionally add password protection and set an expiration date for the link. For more details, view this tutorial.

Faster syncing with Mac and PC. Changes you make to contacts and calendars on your Mac (Address Book and iCal) or PC (Microsoft Outlook) are now automatically pushed up to the cloud every time you make an update. Likewise, changes you make on me.com, iPhone, or iPod touch are automatically pushed to your Mac or PC. As a result, your contacts and calendars update faster across all your devices. To take advantage of faster syncing, be sure you're running Mac OS X Leopard 10.5.6 (Mac) or MobileMe Control Panel 1.3 (Windows).

Improved notifications and sync on iPhone. Reliability of new email notifications and syncing of contacts and calendar with MobileMe have both been improved. To get the best MobileMe experience on your iPhone or iPod touch, you should be running iPhone Software 2.2 or later.

Better web app performance. We have also improved the overall performance of the web apps at me.com including faster start time in Calendar and searching in Contacts. For more details, see this support article.
Remember, to take advantage of these improvements, your computers and devices must be running the latest software versions indicated above.

Setup on a Windows Mobile 6.1 phone (AT&T Tilt) was easy. Just download and install the package from the phone and you can pretty much start syncing from there.

The good news is, sync fairly well for the most part. Contacts, calendar and tasks are synced fine, but so are your text messages, your photos, your videos, music and documents—provided they're all under the 200MB cap. Contacts, calendar, and tasks are two-way, meaning you can create entries right on the web page. Photos, videos, music and docs are upload-able too, which makes this an easy way to transfer files onto your device OTA. Any inconsistencies (a calendar entry created on the phone went to the web fine, but one made on the web wouldn't sync to the phone) can most likely be attributed to this being a beta.

The downside is that this is (by default) only really useful for backing up your phone once a day. You can only schedule your phone to back up once a day or once a week or manually. It's definitely not push and it's definitely not meant to be. This is used for making sure your contacts and other phone data are always backed up, so you won't lose everything in case someone swipes your com.

One good use for this would be to sync multiple phones to the same data. You can attach more than one device to an account, so if you switch between work and home devices—or if you lose a phone—you can just sync up your data again. It's not live-updating push synchronization into the cloud, but it is a fairly good backup solution. [My Phone]

Users will now be able to drop any file into a note which is then synchronized with the Evernote Service. The note is made instantly available to all versions of the app, including the one for the iPhone. While you won't be able to edit those files on the iPhone, you will be able to view, listen to, and even email them. Currently, this feature is limited to Evernote Premium. The service costs $5/month or $45/year if you pay annually. [Evernote via Wired]

With this, the Zune suite itself can take in these files and convert them once into a Zune-playable format. This saves you time, plus effort, since it can auto-scan a folder for new files to convert. Head over to Zuneboards to grab the download.

And don't forget, pink Zunes are almost here. – Jason Chen

Zune Software Hack: Multi-Extension Support [Zuneboards]

Good news for everyone, because all the pre-loaded content stays on the device even after a sync. The bad news? You can't sync the music and videos onto your computer. So you're stuck watching Brittany Murphy cross and uncross her legs in Oakenfold's video solely on your Zune. Darn. – Jason Chen

Zune's Pre-loaded Content [Zune.net]