I've used a variation on option one. I had already made hidden files visible. From iTunes I went to add folder. Then navigated to my iPod, the the music folder and hit go. It imported all of my music and movies into iTunes and back into my iTunes folder in My Music. Not all of it worked right. Several tracks kept the odd naming structure that the iPod used. So a bunch of songs had names like HAGD.mp3.

For option two you don't need a trial version. Get Floola or Ephpod. Ephpod is older but fairly stable. Floola is newer and my personal choice. It's not too hard to use and will transfer your songs with metadata and proper name intact. Both are free. Floola is cross platform and works in Windows XP, Vista and 7. Mac. Linux. Although 64 bit Linux never worked for me no matter what I tried. Ephpod doesn't like iPods that are full or too close to full. Scroll down on the Ephpod page for the DL.