I've blogged before about MediaMonkey and it's a great windows mp3 desktop player appliccation; however i've only really recently gotten the full benefit out of how good it was for syncing music to your mobile with my purchase of the Motorola Droid.
My old htc didn't have the ability to allow direct storage access to the memory card so i had to pull out the sd card and insert into a reader, with the motorola droid all i need to do is connect the usb then on the device itself mount the memory card (it's a one touch process).
After that all i need to do on Media Monkey is click "tools" then click "sync device" and thats it, takes about 30 seconds per gb of music.
As you can see from the screenshot you have a ton of functionality for syncing both mobile specific and non mobile specific playlists.
My personal playlists that i choose to sync to my handset are:
- "1 hour of my 5 star favorites" that were played last (eg i have about 100 cd's that are rated as 5 star favorites and it tracks when i last listened to them, it then selects the oldest listened to cd and syncs it automatically, if i listen to it on my mobile before i sync next it then swaps it out, if i haven't listened to it then it stays.
-"Last 50 played" this one is basically it tracks the last 50 songs i listened to on my pc and syncs these across, eg. Lets say i was in a White Stripes mood today then it will sync this across as i might want to listen to it again when i walk the dog tonight.
-"Mobile Sync" lastly this is the MobileSync playlist, basically any song or cd or artist i right click my mouse on and click add to mobile sync it then syncs these across.
Pretty simple and works great.
At the moment i use Meridian to play the tracks on my Droid, it's ok but could be better. Though software development on Android is such a moving target by the time you read this I'll probably be using something else.