iTunes Agent is a small tool that monitors for devices connected to your system and lets you manage them through an iTunes playlist. It runs in the system tray for ease of access.

iTunes Agent is a tiny application that runs in the background, waiting for devices to be connected to your system. Once a device is detected, it enables you to manage it via a playlist in iTunes. You can even use Smart Playlists, such as "Party Shuffle", to keep your player up-to-date with fresh tracks.
When you're done adding or removing songs from your device's playlist, simply click a couple of buttons to synchronize them with your player. It's that easy! With iTunes Agent, you can enjoy the convenience of iTunes without being limited to using an iPod.
Version 1.2:
Added check for free space on the device before copying
New synchronization dialog has been implemented with log for error investigation
Fixed "Now playing" cosmetic bug when no Artist information is available
Added error handling with retry option in cases where an operation in iTA fails