Best app for managing portable music players

[tawsi]

I'm trying to find an application that makes it easy to manage small portable music players including mass storage devices. Ideally with the following features

1. Ability to sync a random selection randomly tracks from a library or a specific playlist.
2. Capable of transcoding tracks to a suitable format

Do any of the current apps provide these features (with or without plugins)?

[kb3hkg]

I think amarok might be closest since I know for sure it can do some of that if not all.