2$ contest [or smth like that >:D]

i dont think it would work what if its a game you dislike? how will the money be paid? ect

You mean a raffle? I can understand perhaps integrating a mechanic by which a user creates a raffle, people put in their pledges for the raffle, and then someone wins. But that would require a good deal of trust to the users both running and participating in the raffle. Unfortunately, pledging something like that, you'd need a money transfer agent of some kind and paypal takes a cut of money transfers, so the person that collected each 2 dollar pledge would end up with less than 10 dollars.

It would actually be quite interesting if there was a system added that could allow and track say, pledges of TF2 scrap, sufficient pledges made, the raffle runner collects the scrap, marks that they have collected the scrap, and then the system automatically picks a winner.

I could that as a system for people who have very little scrap in their TF2 inventories to pool together for the chance at a hat.

This seems interesting. But yea, there are many flaws to it.

That might be a little challenging to run on a per giveaway basis, but there's always the possibility of running a subscription model in the future. For example, say we had a gold membership that was $2/year. One hundred people sign up, we take that $200, and spend it on user voted giveaways throughout the year. Then, obviously only the gold members would be able to enter those select giveaways. Same concept, same odds of winning, but spread across a larger number of giveaways.

As soon as you start adding money in to the equation Valve will be all over your accounts, as selling gifts is a big no no.