It took a while to think over after reading all these posts (some of which i thought had some good points), but i have eventually decided to take the safe route and start with the Blackwell Bundle first and Psychonauts second. I'll figure out the rest after i've played them.

Thank you very much for the input. ^_^

As most are bundle games on that list and you can get them in future bundles or even in cheap trades if you're a trader, probably not a bad idea to keep them on your wishlist till they come around on sale again.

Hammerwatch should be first. Its new. Its on sale now. If you multiplay, activity on it will be high so you should easily find people to play with.

Those are good games. It's all fall into your own time management. For me I prefer to pick shorter games first to help me keep up the pace. Longer games need dedication and you don't want to get burned out early right?