I just realised I didn't answer the first question about what keeps me from discovering the issues earlier

The quick answer is complexity and the amount of energy I have, since I'm mostly working on my homelab after a full work day

Some things also don't run that often or I don't check up on them for some time. Like hardware acceleration for my jellyfin instance stopped working at some point because I was messing around with OpenCL and I messed up something with the Mesa drivers. Didn't discover it until I noticed the fans going ham due to the added workload