Re: financial support, have you seen Nadia Eghbal's Lemonade Stand for a whole set of ideas:
A handy guide to financial support for open source.
A handy guide to financial support for open source.
https://wiki.snowdrift.coop/market-research/other-crowdfundi...
Has further notes that don't just overlap with the lemonade-stand thing. Unfortunately, Snowdrift.coop is still not available to use itself at this point.