Because it's a disingenuous compare. Stripe is leading you to believe that spending per city resident is a fair measure of the effectiveness of how we spend money. But it's actually spending per homeless city resident that's the correct measure of that!

SF has a much higher rate of homelessness than the national average, so that explodes the per-resident cost. But we actually spend less per homeless resident than NYC. Surprised?

Stripe knows all this. They have this veneer of plain spoken honesty, but take note of the trick they're trying to pull here.