Say it costs $0.75 USD to ask a noob question. The answerer receives $0.50 USD of that. The asker gets to pick the person who answered them best, and failing that, upvotes would decide whom the spoils go to.

It would be easy to game such a system. Ask your question, get the answer, have a sock puppet account also post that answer, pick your sock puppet as the winner, only pay $0.25 for your question to be answered and stiff the person who actually put the work in to solve your problem.

If it were upvote based, people would have multiple sock puppet accounts to upvote their sock puppet answer.

Adding money into the mix makes it more difficult by a massive order of magnitude. Stack Overflow could open a paid noob question area and profit immensely from it, but a newcomer would first have to build the audience, get participation, and then introduce the payment system while working constantly to guard against sock puppets ruining the system.

Anyway, if you are going with this, billing by the question and gathering your answering team by random are sure ways to break it. You have to somehow limit the amount of questions people can ask, have long term relationships with both sides, and make sure the asking ones won't expect that every single question can be answered.

Personally, I would bet on Stack Overflow being positioned in a way where trying this would certainly fail. It looks way more likely that something like a "Red Hat School" could do it.

(But when one can make a comment saying "I know who can enter this market! It's IBM!" that's clearly a problem.)