MattK

Red Dead Redemption first. Assassin's Creed II is a big improvement over the first game, so play that next. I  found Alan Wake to be a bit disappointing since I was expecting something more than a straightforward corridor shooter.

Pretty much always do, and in the event that I don't, I just buy it at the post-Christmas sales anyway.

It's never too late, and GoG pretty much kills the compatibility issues for the best games. The only real issue would be the steeper learning curve (compared to the hand-holding of most modern day games). Cannot recommend Fallout and Fallout 2 enough.

2007 VW Jetta TDI.

I'd rather see a larger content pack than cheap piecemeal DLC. Might be a bit more significant to me if the guns in ME2 were a bit more varied.