Thanks for all your input! As mentioned in this related discussion, we do already have some large organizations interested in using and/or supporting LibreTime. I think integration and support of plugins like Radio Station and the Drupal Station module (upgrade or total rewrite) could be sustained with a similar mix of crowdfunding, partnerships and services.
I’m less familiar with how WordPress developers are incentivized, but generally speaking, I think budgeting for a good PM and sustainer (fundraising, sponsor wrangling, managing crowdfunding campaigns etc) would enable development and maintenance of all the related plugins and integrations.