I have a 1st Gen shuffle. In order to use it on Windows 98 I had to create a 'false' iPod database by downloading the directory/folder/file structure from a zip online. I then used my iPod like a USB flash drive (by downloading the drivers) and had to manually rebuild the database everytime I added songs.

I now have a new (finally) computer with Vista and want to install iTunes and use my shuffle like every other person. Do I need to delete the current structure on my iPod? Should I reformat it? Does iTunes automatically update my iPod firmware?

This is kind of a reverse process.