The ability to rip dvds like you rip cds
now I know(at least in the US anyways) this isn't going to fly because of DMCA and whatnot, but right now I am in the midst of a massive project to rip and categorize all my tv show dvds. Right now I go through handbrake, then import the shows into iTunes, set them as TV shows, give them the correct episode name and number, and I even write descriptions for them(like they do for the shows you buy on the store). It can be a lot of work, I wish I could just pop a dvd into my macbook and drag it over to my library like a cd, and the rest of the info would be filled in from Apple's database.
Also, better ways to sort TV shows would be really nice. Right now you can only have them in either a giant list, a giant list separated by show, or cover flow, which is almost meaningless for TV shows anyway. It would be nice if we could do what we can do for songs, ie pick an show, then see a list of all the shows on the bottom, and in the upper left see a list of seasons. and if you click on one of the seasons you only see the episodes that belong to that show that season.
I own all the released Simpson dvd sets(and am planning on adding more as they come out) and my collection of Simpsons episodes is getting unruly.
Also, it would help if we could sort things better in front row too(not strictly iTunes related but....)