I agree with all your points, but I'm still optimistic. The biggest two issues are that anything related to finances is heavily regulated, and that third-party

I agree with all your points, but I'm still optimistic. The biggest two issues are that anything related to finances is heavily regulated, and that third-party services integrated into repositories/blogs/posts create lot of friction for users. It should come down to 1 button: donate fixed amount immediately. It's easy to press that button few times, or to press the button every time you update to new version. Simple is good. One way around regulation would be for each online service to have a independent credit system. Like karma, but you can also spend it to reward others. Communities would reward each other for creating content. Independent entities could offer to exchange your GitHub credits to Reddit credits. Those entities could also handle exchange to and from actual money, with credit card fees and necessary financial regulation isolated to just those entities. Let the market regulate itself.