I think it's all about optics... 5000 people paying $20 is probably easy to manage in a "I'll do something awesome this year, trust me" model than 50-100 "Let's raise money for this tiny feature" pledge drives.
But... It would be really nice if it were a thing... Possibly there is a better way to represent it that makes it more appealing to payers.
Only in a few parts of the U.S. with sky-high cost of living and rents. Most FLOSS developers are not in such places. (OTOH, high costs are definitely the reason why there's little-to-no "pure" crowdfunding for things like AAA-class video games, or live-action feature movies. It turns out that the cost of these things is so high that, by and large, people aren't actually willing to fund them when the full cost is made transparent.)
There is potentially a third way: crowdfunded bounties. There are some sites for these, but they don't seem to have attracted much activity. (I built one myself a few years ago, but dropped it when it didn't get any traction.)