Wikipedia is shady at best about how much money they actually need from the community. Reddit does not internet to receive people into giving up money. The recent push to giving gold sounds pretty cool.

Totally random idea, but maybe they could offer support for paid, private sub-Reddits and take a cut. There are a few I'd pay (a small amount) for.

The userbase would balk. Private subreddits are already a feature. Asking users to pay money for something they currently use for free would tick off power users who have ungodly influence among the users. I think I get what you're talking about, but Reddit is not like Github enough to pull that off.

They do have that feature and it's free.