Not sure if I like this idea. I myself do not have a horse in the race so to speak (I don't advertise my games). But the idea of 'pay to win' GM/DM ads unbalances the purpose of the LFG space. Plus it would be playing 'favorites' in one particular part of the site for certain users that is reflected no where else. (No where does do Pro or Backers get higher ranking/featured posts than anywhere else). It plays into a misconception some users would see that "This is a better/more popular game" because they spent money. Which may or may not be true on the better part, but they are independent of each other. I think (or at least hope) that while Roll20 is a business, and has a business model of making a profit, that the concept of 'A more featured GM depending on depth of wallet' never becomes one of the business practices. As then the top of LFG area would be dominated by the pay to play GM's looking to maximize exposure. Not that pay to play is bad to each their own. But being able to usurp all the other ads for that cause would not be a positive addition to the environment. It would be mixing two separate groups, that peacefully exist on their own (paid vs free games), into one area with one having the clear and purchased advantage over the other. It opens a door that might not be beneficial to open. And at least for me if I was looking for a game, I would skim over the paid ones much like when searching google and passing up the 'google sponsored ads' at the top. (And I think any paid ad would need to state it was paid for, for transparency). I personally believe a better approach for you would be to reach out to Youtube GM's to sponsor, outside advertisers on RPG sites, and such so Roll20 and its site stays agnostic in the situation of your popularity. Now if Roll20 decided to partner with you, that's a different situation. As they would be teamed with you, vs you buying popularity and exposer.