Thx a lot for sharing.
I'm a 50+ non-geek Linux user myself, and selfhosting is the one computer 'thing' I would love to be able to setup one day but I'm too afraid to seriously start doing as I'm way too afraid of being that 'low hanging fruit' you mentioned in your post.
I said I was not a geek in the sense that, after almost 40 years using only Apple computers, I've switched to Linux to use it like I used... my Mac. Sure, I've learned to understand a little bit of Linux workings and I would not want to go back to the Mac, no way, I can also write simple bash scripts (with a lot of trials and errors) but that's about the full extent of my computer 'expertise'.
So, even though your post is well written and informative, it was still way beyond my limited skills, I'm afraid. I'm not saying that as downer, it was a really interesting read and very informative with all those useful links, but hopefully as away to let you know there are... extremely... odd users like myself that are very much interested in the idea but also are as clueless as an oyster comes the time to buy a pair of sneakers :)
In regards to self-hosting, my conclusion so far is that it's a much safer choice for someone like me to not do it. The risk is too real to get into some serious issues. And that I'm better off using the few paid services I rely (all in the EU, many of them small companies I can have have direct/human discussion with) as I know by experience I can trust their expertise a lot more than I woudl ever trust my desire to ever become not completely in competent in those fields ;)