@Kevin Eklund -

I should probably clarify: I am absolutely *not* in favor of a mandatory "donation" (if it is the former, it is, by definition, not the latter) model for WordPress plugins.

I'm all for some plugin developers putting together their own for-pay plugin repository, if they so desire; however, I think that approach would be detrimental to WordPress in the long run.

Now, if every plugin developer wanted to create a for-pay support system, I'd be all for that, too. That approach would allow developers to set support rates commensurate with their time/effort spent on plugin support.

At the same time, perhaps I'm too idealistic, but I think that the right donation system could prove to be a significant means of compensation for developers - again, if it is optional, visible, and convenient.

I would posit that part of the problem right now with the donation model is that the plugin author donation link is on the Plugin's repository page - somewhere that is rather seldom visited by the vast majority of plugin users. (Once plugins are installed, the repository listing becomes out of sight/out of mind.)

I would imagine that it should be rather easy to pull that same donation link into the plugin's listing in the Plugin Admin UI - or if not, how difficult would it be for Automattic to expose it through some sort of API?

And once the donation links are listed for all plugins in the Plugin Admin UI, I would imagine that one of the e-commerce plugin developers would have both a good code base - and also, great incentive - to develop a plugin that would facilitate the plugin donation process, both one-time donations and (the ultimate goal) recurring donations.

Then, start a community-driven effort to increase use of such functionality. Start small: ask community members to volunteer to set up recurring payments of $1/plugin per year, and set a goal of 10% of all WordPress installs.

What would critical mass be, for a self-sustaining donation system? I'm guessing that it would be even less than 10% of the userbase.

A quick look at the top 75 most popular plugins (according to the repository) shows almost 50 plugins with 100,000 (or more) downloads - up to and including AIO SEO, which has over 2 million downloads. Getting a $1 donation from 10% of the userbase would bring in between $10,000 and $200,000 (each) for just those plugins alone.

Is it possible? I think so.