well yeah, you should be familiar with the services you host, means you are competent with them, and are capable of fixing things when they explode.

I mean, would you rather have spent 50 hours learning and setting something up, becoming somewhat familiar with it, vs clicking a button and it runs. In the event that it explodes and you need to maintain something?

It's a price that's worth paying for, not to mention it's not like you've wasted that time. It's time that you can use to put into other things that will benefit your life. I am currently running about 4-5 services, aside from game servers, that directly benefit my life. Because i've taken the time to learn and understand that stuff. (all of which are free, and run on my own hardware)

Plus it gives me freedom, i'm confident and content that i could self host every service i would need to use, in the event i dont want to use outside services. It wouldn't be pleasant to learn and or setup, but i absolutely could.