Unless you use Windows Media Player there is not an easy
automatic synchronization option available for an Android
device. I personally use the amazing Songbird
media player, and have wanted the ability to sync a Songbird
playlist to my G1 for some time. I finally found a simple solution
thanks to the Songbird add-on FolderSync.
This solution will also work for any device that will get a
drive letter assignment when it's connected to your computer.
Install/Update Songbird
Grab the latest version of Songbird from http://getsongbird.com/.

Install the FolderSync Add-On
You can also install the FolderSync Add-on by clicking
here if you are viewing this page from
Songbird.
Open Songbird and select Add-ons… from the
Tools menu.

Click on Get Extensions in the lower right portion
of the screen. This will open a new browser tab in Songbird.

In the search box on the upper right of the page, type
FolderSync and click
Search.
Locate the FolderSync Add-on and click the green
Install button on the left of the page.
Restart Songbird after installation is
completed.

Create/Select Your Playlist(s)
From the library tab in Songbird, create a playlist. Use the
library views to drag songs, albums, artists, etc from your library
to your new playlist to update it.
You can also use an existing playlist, or multiple lists. The only
limitation in the case of is the available memory on the
device.
Configure FolderSync
You can view the complete (and most up to date) documentation
for FolderSync here:
http://wiki.songbirdnest.com/User:Rsjtdrjgfuzkfg/FolderSync_Manual/FolderSync_Manual_English
From Songbird select Add-ons… from the
Tools menu.

Locate the FolderSync entry and click the Options
button.
Set your preferences in the options screen, for FolderSync 1.3, the
following options are available:

- Activate one-click synchronization of more than one
playlist: Check this option to enable the "Sync All"
button.
- Delete not needed Files and Directories: Check
this option to delete all files/folders as part of the sync
process. I highly recommend you un-check this
option:
Important Note (hence the red text): DO NOT set the
destination folder in the sync to the root of your device/sdcard
with the Delete option checked. If you do, ALL OF THE FILES IN THE
ROOT FOLDER WILL BE DELETED.
- Write M3U-Playlists: Check this option to
create a single m3u playlist (per Songbird playlist) in the
destination folder.
- Auto-format filenames and path: This option
mimics the iTunes/Songbird music organization feature, but allows
you to control the folder/file structure. I have mine set to
this:
%artist%/%album%/%tracknumber% %title%
An example result of the above format would be: \Music\Alice In
Chains\Dirt\1 Them Bones.mp3
Click Save to update your preferences, then
restart Songbird to apply the changes.
Set Up A Sync Partnership
If you haven't done so yet, connect your device to your computer
and mount your SD card.
To view the FolderSync interface, select Show Content Pane
Bottom from the View menu.

If you have multiple Add-ons installed, you may need to switch the
bottom content pane to folder sync. To do this, click on the menu
icon on the top right of the content pane and select
FolderSync.

- Place a check next to each playlist (in the left pane) you want
to sync to your device.
- Click the button labeled Browse and navigate
to the Music folder on your sdcard.
- Check the sync folder on the right pane.
- Click the Start Sync button to copy your
files.

The first process may take some time depending on the playlist
size.
The setup takes more time than anything, and the only
enhancement I would really enjoy at this point is the ability for
the sync to happen automatically. Since this is a file system-based
solution, I understand that auto-sync can't really mimic the WMP or
iTunes style of synchronization.
I hope you find these instructions useful… be sure to post a
comment or any questions you have. Happy syncing!