I can relate to many of the frustrations. As years have passed, I've been trying to lessen the (repetitive) effort required for basic monitoring and maintenance

I can relate to many of the frustrations. As years have passed, I've been trying to lessen the (repetitive) effort required for basic monitoring and maintenance over plain SSH. I felt that just the shell wasn't good enough, and large software stacks just increase maintenance burden. Ended up creating a GUI app called Lightkeeper (https://github.com/kalaksi/lightkeeper https://github.com/kalaksi/lightkeeper). Works over SSH, requires no daemons and is configurable. Still working on some unfinished features.