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Indeed, seems like it should be pretty straightforward.

I understand why the venture-backed entity couldn't do this, but given the reactions here, could a new maintainer not take over and simply charge for support and future enterprise features like the Sidekiq guy?

Developers as well, all other professionals pay for their tools.

If only those that boast online how X is greater than Y in every single thread, actually paid even a Starbucks coffee to X.

Maybe but only if that gives them a competitive advantage.

There's no reason companies can't fund mutually beneficial entities. In fact, it's quite common in the form of trade associations.