I like the idea, and "actionable paid insights into the future of this tool we depend on" might be a good sell. But maybe don't make it a subscription, one off

I like the idea, and "actionable paid insights into the future of this tool we depend on" might be a good sell. But maybe don't make it a subscription, one off payments can be easier to get approval for even if they occur every year. Another thought: Often devs have a yearly budget that can be spent relatively freely on training/conferences/courses/books/etc. Conferences and travel are expensive, but with everything going on it's not being used as much. I'm sure people would pay to get on a Zoom call or Q&A with a few core devs if it comes out of that budget. Price it pretty high, perhaps a few hundred $ per participant, maybe add country-dependent pricing or make exceptions for OSS projects/etc. Basically a fundraiser with a training/conference talk component.