Thirded (or fourthed...) about GH titles. They look really cheap and nasty on the shelf. The current gen ones all look bad (can't decide if GC or PS2 are worse-looking). I normally buy used games anyway, so I try to pick up the originals.
I'm the same way about CD's...I always think "Why would I buy a band's Greatest Hits...Why not remaster the original CD's and re-release them instead?" Well, I know why (cheap impulse purchases for less-informed buyers), but it's really lame if you want everything a group has put out and the originals are out-of-print or have that weak 80's initial mastering done. Greatest Hits that get all the tracks I actually want are a rarity (I was really annoyed the Def Leppard 2-CD one lacked my favorite song of theirs..."Stagefright", if anyone cares). I'd much rather have paid $10-$12 apiece for remastered editions of Pyromania, Hysteria and the other CD's they plucked from.
Also, I always use the classic winamp skin. The newer one is absolutely unusable and an eyesore. I got used to the newer iTunes though after a couple sessions. Having it out of date made my iPod act funny after I tried to sync it (it read empty space as being full of music, would reload EVERY piece of music instead of only stuff I added) and I think the newer one makes it MUCH easier to reset an iPod if it acts funny.