I have a Macbook Air (10.7), a Verizon Pre 2 (unhacked). This is how I create playlists on my phone. I haven't figured out how to use Wifi Media Sync to get it to sync new songs and playlists yet, but that will be my next step...

1. Plug phone (USB) into Mac.
- Select USB mode (I have media sync disabled)

2. On the laptop, open the PalmPre drive
- Create a Music folder
- Copy the contents of your music folder to this file

NOTE: I have all my laptop music under a Music folder. In that folder is and iTunes folder, an Amazon Music folder, and actual mp3 files and may look like:

/Users/FlyFrosty/Music/Amazon MP3/Neon Trees/Everybody Talks/01 - Everybody Talks.mp3

3. Open iTunes
- Right click (I think it's control left click if you don't have the right click enabled) on a playlist you want to copy
- Select Export
- Save them somewhere easy to find (I save them to my desktop)

4a. Using TextEdit
- Open TextEdit
- Under preferences and Open and Save tab, make sure the Plain Text File Encoding is set to Western (Windows Latin 1)

NOTE: You only have to set this once

- Select (from the top bar) Edit, Find, Find and Replace

NOTE: You may need to Unlock your file at some point. That is fine.

- In the find window, type all the directory stuff (in my case, "/Users/MyName/Music/" )
- Leave the Replace window blank
- Select "All" to the right of the Replace window

NOTE: Goes from:
/Users/FlyFrosty/Music/Amazon MP3/Neon Trees/Everybody Talks/01 - Everybody Talks.mp3


Amazon MP3/Neon Trees/Everybody Talks/01 - Everybody Talks.mp3

NOTE: The EXTINF lines are standard playlist info and don't require modification.

- Close TextEdit. Mac Lion automatically saves a new file for you…

4b. Using MS Word

NOTE: I can't get Pages to save as a Western (Windows Latin 1) file, so I don't use it.

- I'm not going to go into details, but to open the file, you need to select other encoding and select the Western…
- Be sure that when you save, you select the text format, then change the coding by selecting the other bullet and the proper encoding.
- It may try and force you to use a .txt. If it does, put both the m3u extension on it, then after you close the file, delete the .txt part.

5. Copy the playlists to the Music folder on your Pre. It must be in the main directory. The Pre is very specific on file structure and the file path to your songs must match up with where the playlist is located. You can use the file manager to make sure the directories match-up.

6. (This may seem odd but…) Re-name your music folder on your Pre. Call it Music1 or something. This will force the phone to re-scan your Music folder (a process that will take a couple of minutes)

NOTE: Sometimes you may need to restart your phone to get this to take. Sometimes it works without re-naming the folder. Go figure…

Sounds complex as I read back over it. But I can buy a song off Amazon. Download it to iTunes (Amazon MP3 Downloader does this automatically for me). Add the song to my playlist (Gym). Export it, correct it, copy it and play it in just a couple of minutes. The long straw is finding my USB cable.

Hope this helps...