Often wondered if github could add a commerce layer.
- Bounties for wishlist issues.
- Check-splitting autopayments to support the libraries going into your build.
- Kickstarter funding for hitting a milestone.
- Paid subscriptions/underwriting for libraries used (with some of that going upstream to the libraries they used).
Experimentation could help us find an appropriate mix of models.
A slightly more difficult challenge is extracting the non-financial signals that a specific body of open source work needs attention. Either that it is putting existing dependencies at risk or that potential opportunities will be missed without intervention. This is a general problem, not necessarily a funding one, but addressing it well would serve your initiative.
One of the barriers to solving the signaling and funding problems is that nearly all of the data we can find is on github and a handful of other services. The rest of the iceberg is behind workplace firewalls. Exposing the dark matter of open source use is another great challenge.
Good luck. This is important work.