[James]

DMC 2 was described as emabrassingly easy.

You can get GTA3 and Vice City as a pair for Greatest Hits, and starting with 3 and working your way up to San Andreas will help you get into the swing of things. Each game is HUGE, and each game is FUN. It'd suck to just jump to San Andreas, because then the previous games just aren't as fun to play, and you'll miss out on two great experiences.

VF4: Evolution ONLY came out as a Greatest Hits game. It was released for $20 because Sega is awesome like that. Besides, half the games on your list you'll only find as Greatest Hits unless you buy them used. I'd also suggest less intense fighting games, like the upcoming Mortal Kombat: Deception or Tekken 4. Just because VF4 can get VERY aggrivating with its steep learning curve.

I'd also suggest Dark Cloud and Dark Cloud 2. Since you seem to like RPGs and action/button mashers, these games are a great mix, with some wonderful features mixed in.

Other things worth note: Jak & Daxter, Sly Cooper, Ratchet & Clank, Jak 2, Sly 2, Ratchet & Clank: Going Commando, and eventually Jak 3 and R&C 3. The first Jak & Daxter is pretty "by the books" in terms of gameplay, but it's fun, but you can still skip that. Sly and Ratchet are GREAT platformers (coming from someone who HATES them).