How well does painted upholstery hold up?

Hi there, I have never done it, but I have seen numerous DIYs over the years, some even updated to show how they've faired after use. This post seems to give you an idea of how each paint works and wears, perhaps it will help you decided on a method. https://www.apartmenttherapy.com/diy-project-test-lab-results-we-tried-3-fabric-paints-on-upholstery-and-heres-what-happened-218302

There are many sites discussing this very thing. I am sure it will do well for you...

https://www.hometalk.com/diy/kitchen-dining/q-how-does-chalk-paint-hold-up-on-kitchen-cabinets-6090020

https://www.11magnolialane.com/tutorial-how-to-paint-upholstery-fabric-and-completely-transform-a-chair/

Fabrics, depending on the fibre content and finish (both the right side and backside), lend themselves better or not-as-well to being painted, and have more or less durability over time.