The only type of person who would use the iLoad by Wingspan is the person who either hates computers or doesn't know how to use them. The device takes in your iPod, then rips CDs into digital form and loads them onto your iPod. No PC required.
Crunchgear took one for a spin, and thought it worked as advertised but was super noisy doing it. Once your music is transferred from the CD into your iPod, you can also delete tracks by title or category—again, straight from the iLoad without a PC.
Is it worth the $299 price tag? Only if you're an anti-computer guy who still wants access to an iPod.