I think the biggest obstacle are the "getting started", and then "actually owning it" parts. I registered my domain with Gandi (who have also initially hosted my email), got a VM from Hetzner, set me up some nginx, and I was good for a while.
Then Gandi dropped their "no bullshit" motto and wanted €48/y to renew a €12 domain; I transferred it away to MrDomain, plugged my email into iCloud, and since I didn't actually need a VM, Netlify is now my web host (with Hugo as the blog engine). Now I want to move away from non-EU companies and facing another crisis.
The fact that you can do it at all is a welcome sign for individuals who desire digital independence. But every step of the way, I needed sysadmin expertise, and also now have to shop around for a whole bunch of new providers.
What is a DNS record? Why can't I set up CNAME on a naked domain? Why is it so difficult to find out the correct IMAP/SMTP settings? Why do I need a PC, a text editor, and git to publish a link with a 20-word comment? Why is $PROVIDER integrating with Github only, while git has always been non-centralised?
There has to be a better way. There are countless providers that will offer you a DNS+email+web hosting package, but there will always be shortcomings (e.g. running a blog engine that is not Wordpress; Wix is impossibly slow and clunky; etc), and moving to a different provider is pure pain even for experts.
And then, self-hosting even the most basic apps, like an RSS reader, bookmarks, calendar/TODO? No providers will get you the full package, you have to resort to a VM of some kind and do the expert-level twiddling, likely including setting up Postgres somewhere along the way. Assuming you have the knowledge: cryptominers destroyed the free tier on anything that needs compute; it doesn't matter if you need 30min of CPU and 100MB of transfer per month, you will end up with a bunch of extra bills and several moving parts.
You could argue that gardening also requires knowledge and maintenance. But free software and open protocols are about reusing existing building blocks. You never ever had to write an email client.
I want the experience of installing stuff from the App Store. I want the experience of changing web browsers, where the new one just imports bookmarks and history from what you've been using to date. Even if it's adversarial compatibility.
It should not matter if I'm a noob or if I've been a sysadmin for the past 10 years. Even if the latter is the case, I still value my free time, and don't want to take my work back home.