Tried the same some time ago. While setup is fun, maintenance etc. is mostly underestimated. Following Murphy's law, things mostly break in uncomfortable times (deadlines, etc.).
My (current) strategy: Do without the "last functionality" and stick with boring, local software/approaches. Not everything needs to be synced to / accessible from any device -- at least for me... One well backed-up machine, a few online services (e-mail, github for collaboration, ...) and long-proven applications like Photos.app. Something close to the situation 15 yrs before?