I will say, I didn't realize the funding situation was _that_ dire, especially since on Talk Python I remember specifically Michael and some others talking about the massive influx of money into Python and its ecosystem in the last year and half or so. Its not billions of dollars but it sounded like the situation had a positive uptick substantially, so, in short, I was wrong!
Has the PSF ever considered having an actual business? Like say, consulting and/or having developers work on features that businesses pay to have implemented? (A loose example of this would be Igalia[0], which makes surprisingly good amounts of money to implement features in web browsers on behalf of the major browser vendors)
I've always thought this would be a pretty natural way to have a steady source of revenue and the profits could all feed back into the PSF.