I can't personally recommend any of the software, as I've never used it with an iPod. The closest I've come is using Notmad Explorer by Red Chair Software, which also makes Anapod Explorer. Notmad Explorer is for Creative's players and supports drag-and-drop loading of songs onto the player. Anapod Explorer looks identical, but for iPod instead. It is Windows only, which may be a downside depending on your situation. A free trial is available for download.
I would also like the ability to just drag a song or two onto an iPod just like I would to any other hard disk, but I'm sure Apple had dozens of reasons for making it more complicated than that.