Replying to myself to add...
This was all while installing this and that dependency and troubleshooting it. Docker was a complication I didn't want to learn yet.
And then tinytinyrss moved to docker only which forced my hand. I can say installing Docker and Portainer (as someone who prefers a GUI more than command line) has made self hosting so much easier for me, and hugely reduces the need to think about dependencies.
Absolutely. I had a similar journey. I started with Yunohost and DietPi. Then plain Raspbian, then plain Debian. Each time nuking and starting from scratch. You learn quickly when you've got to retrace the same steps again on a fresh install after messing something up.
Eventually, I tried and stuck with Proxmox (running a Debian VM) and Proxmox Backup Server. With that, you have your regular backups, and if you mess up, you simply revert to a previous backup version.
Others will recommend Ansible - I haven't got that far yet.
I use Google Assistant a lot. I tried the Gemini Assistant on my phone and it was an exercise in frustration.
Me: (after pausing the tv) "Resume TV"
Google: (resumes playback on TV)
Gemini: "TV not recognised. Please say the device name" or even worse... "A resume is essential when you're looking for a job in television. Your resume should blah blah..."
Me: (with phone locked) "set a timer for xxx"
Google: "setting a timer for xxx, starting now"
Gemini: "I'm unable to set timers, please unlock your phone, open xxx and (lengthy step by step instructions)", or "setting a timer for yyy" (completely wrong time).
I ordered one of these off Ali Express. An oscilloscope app showed it was about 40Hz vibration from the weight on the motor, far far from being ultrasonic. Got a refund, it ended up in the recycling.