My iPod ran out of ziggurats! Help!

[الله أكبر]

Actually, I have legit questions about iPods. Since I am using iTunes for all my music-listening purposes now, I am considering (hell, I'll probably end up) getting an iPod at the end of the summer. My DellPod suffices for the time being, but I have the first generation one which is very choppy and needs to be restarted more often than I'd like to have to. My questions are these:

1) Can any major update to the iPod be expected in between now and mid-August?

2) I spent a fair amount of time manually entering song data into iTunes (like artist, album, etc) for files which had no such information (or it was all in the title, for example "Metallica-Master of Puppets-01-Battery" as the title). If I get an iPod, will this data transfer according to my iTunes, or according to the actual file?

[Violent Unrest in Allentown]

1. My guess is an iPod update come early to mid summer. Which might work out, because that means the old ones become very inexpensive. I really have no idea what they'll add to the iPod - other than totally revamping it with wireless capabilites or some other high tech gadgetery shit. Color + authentic iPod feel = 5th gen very awesome music player.

2. It will transfer according to iTunes.

Now everyone post pictures of their iPods! (I don't know what that spot is on my pillow, but that's pretty gross.)
My Black 5th-Gen in its Marware CEO Case.

[الله أكبر]

Here's mine:

[الله أكبر]

Fuck this fucking image scaling. I don't listen to shitty bands like "Omniocmmi€ cal Mil ;"