If you're going to start to get into AC you should go for 2. 1 was more a proof of concept game, though it is better on the PC than the original console versions as they included more quest variety.

Here's what I'd recommend based on type:
Strategy\Politics - Crusader Kings 2
Simulation - FTL: Faster Than Light
RPG - Legend of Grimrock & Torchlight
Puzzle - VVVVVV
MOBA - Awesomenauts
Adventure\Horror - Amnesia
Adventure\Story - The Walking Dead
Adventure\Puzzle - Monkey Island
Action\Puzzler - Hotline Miami
Action\Platformer - They Bleed Pixels

That should be a good starting point. :3

Yeah I'm staying the hell away from Amnesia. Haha. 10 minutes of the demo was plenty for me.

And yeah I'd noticed a lot of games tend to be:

I - Playing around with a new concept (portal, splinter cell)
II - Stuff a multiplayer element in there (again, portal & splinter cell)
III - Kickass Awesomeness

Thanks for the suggestions!

I like your hat.

My hat is awesome. U.U Thanks!

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Depends whether you care about the story or not. If you do then get all the games and play from the beginning like they were made to be. If not, skip to no.2.