And what I'm saying is: that's exactly what LLM's are super useful for.
To answer your last question: about every 6 months or so. I'm a freelancer, I do a new project for a new client every 6 months on average. All of their toolchains, build systems, OS of choice for the dev machine, OS of choice for the SoC, documentation methods, PCB design tools, version management systems, release systems, testing frameworks are completely different per client and change constantly (even within the same company) depending on department and moment in time.