Update, I figured out a solution!
What was my solution? AI.
I’m dead serious. I went full-on agentic and had the agent set it all up for me. All my “fleet” devices auto-update; they auto-configure eth0/wlan0 based on which is connected; they run whatever they need to, and the agents figured out how to add whatever scripts they needed.
If I provision a new device, I literally just connect it to the network and tell the agent to “go”. It has markdown files with sets of instructions that it self-maintains, and that’s how I’ve expanded and maintained my 32 Raspberry Pis!
AI’s the way to go! I don’t have to do any of that tedious stuff I never liked, and the agents can figure out how to make sure updates are occurring as they should.
Once you get it all figured out, you never have to think about it again. “Oh, something stopped working?” Have the agent fix it.