It's interesting that you mention a feeling of "tackiness" with respect to directly funding something via a bounty system. Although my personal project [1] isn't necessarily about providing incentives to open source software development, I did recently launch a new subsection focused on motivating businesses to act out of a motive other than the profit motive alone.

The motivational approach I took was slightly different than crowdfunding. Instead of directly funding the tasks you want to see completed, the bounties are donations to charity made on behalf of the tasks. They can be either made immediately to establish your level of seriousness or made when the task completes, to provide ongoing motivation.

Since I am focused primarily on motivating city governments and businesses, I felt the same way as you: direct funding is not the right thing to do. These governments and businesses already have funds. If I want to sway their decision-making processes in some unusual way, my experiment is using public charitable donations.

Just as a demonstration, I just created a task for this (admittedly, not really what I have in mind for my site, but I'll take whatever eyeballs I can get) [2].

[1] https://www.brianstaskforce.com/

[2] https://business.brianstaskforce.com/task/385/oracle-address...