@Kerry I have a decent collection of boxes running different stuff… Plex and controller for my Ubiquiti’s wireless gear on one, PFSense (in process still) on another, NAS hardware and a Pi or two for giggles. The big server will at some point be a VM box that some of the stuff will get moved over to but not until I learn more about virtualization software. No need to artificially inflate my power bill at this point.lol
I’ve got some Linux experience by virtue of being to poor and/or cheap to buy Windows for anything that doesn’t come with a Windows licence out of the box, but mostly just enough to get me into trouble and not enough to get back out of it.
Like yourself, @Guru_Of_Nothing, I’m a guru of very little. When I first tried Home Assistant I noped right out of it because my coding experience extends to Hour 3 of a Sam’s book. I tinkered with a few others but found them either lacking device compatibility (pimatic) or the GUI to be less intuitive than HA’s YAML-based config (OpenHAB), so I gave HA another chance. Turns out the YAML combined with their excellent documentation is actually very simple.
I’ve found the best way to run it is on Docker. I started using their Python Virtual Environment which was was fine until the next update, then it was a bastard to update so I moved to Docker. I tried HASS.io when I moved it off my server onto a Pi but had numerous issues and gave that up (looks like you’ve got it working for you though, so great). Now I run on Docker on Raspbian Lite on a Pi3B+. With Docker it’s self contained, simple to update, simple to back up, simple to move to new hardware. To run the container on startup, use the the docker run command per the HA installation docs but add --restart="unless stopped" to the command. No messing around with systemd, it just works.
If you have a Spare SD Card, Try giving HASS.IO another shot i don’t know when you tried it last but they have made huge improvements over the last 2 months. It got lighter / Supports 64bit devices a lot better and got way faster on them. And there iss the add-ons. They have mad huge steps for them too you know have ingress. an some (not all for now) add-ons will support ingress. Oh and you have automated snapshots aswell
Well, I have become a pro at installing Hass.io 
I installed it once and started to get things dialed in and then I did something with Sonoff’s and addressing and couldn’t work out how to properly fix my mistakes and broke it. I reinstalled and started putting the add-ons back in that I wanted and messed up the configuration… and broke it. I reinstalled it again, got almost all the add-ons dialed in just the way I wanted them and had my Sonoff gear working flawlessly (and made a config cheat sheet JUST IN CASE I screwed it up again, which was fortelling prophecy because)… then I broke it 
The last time was because I deviated from my plan and changed the password scheme I had and then couldn’t remember what I had used (cuz I didn’t put it in my cheat sheet, DUH!) and could not figure out how to get into the directory I needed to get in to edit the password out. So it was easier to just restart, especially now since I could do that part in my sleep, though sleeping while doing it has proved to be problematic, obviously. Still not sure I am 100% OK with it’s functionality yet but it seems to be a lot less work to get “things” working from the get-go. And I had plans to do a A-Z tutorial on how to get something started to take some of the “daunting” out of the process… but I am so deep in the weeds now that any tutorial I did would require many videos. Not sure I will be headed down that road now.
Sounds to me like you’re just having too much fun with this.
I keep a mediawiki server running locally to make notes on about all kinds of things. It’s got to the point that I have a habit of copying & pasting from my own server to set up new machines. (I can SSH into a new server install & configure it without actually typing anything in now…) One of these days I’m gonna have to make it public & see how popular it gets.
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That is exactly the direction I went. Well, with a Word doc titled “The Big Black Hole Network Bible”. It has ALL the data on my network, IP’s, computer info, software keys, and now a section of cut and paste setup code that I can paste into place for easy reconfig when I brick something. I am printing updates now, about every other week or so, just because I need it for the reference. Jon’s video on what should be done to future proof your network setup should you pass on made me think and then I realized I could not remember the vast amount of data I have installed in here.
I went the wiki route so I could access it from anywhere without needing to bring the file along. Also because it would have ended up being either a massive, complicated document or a whole drive full of files.
One rather nice benefit, I have a few friends & family that have found it useful and even contributed to it.
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