Wow great list. When I have the time, I try and self host as much as I can. I’m not aiming for 100% of everything to be self hosted and still rely on SaaS products. You would need a lot of free time to go fully self hosted, and a lot of patience when things go wrong. Also you would need to fund several VPS instances and not everyone has the disposable income for that.
I feel it teaches much more about the hard problems of IT administration, and the state of tooling in that particular space.
Why would you need to fund several VPS instances? I don't understand.