I am happy to announce that I have gotten my systems up to the point that they are running almost entirely on autopilot. Part of it came with a little training of myself as well, mostly to not mess too often with the computers. Due to power concerns I am running my least efficient machine only on weekends, and my highest powered machine, which is incredibly quiet runs most of the time.
Every Sunday night I run updates, and each morning before work, each day after work, and then every evening before I go to bed I check to make sure things are running without issues. Its a simple processes that actually takes very little time out of my day, and has been working like a charm.
To do Still: The main thing I need to do is resetup SSH capabilities into my machines. While not hard I feel as I moved around the ethernet cords in the router, the IP addresses changed so I need to go back in and figure out what they are and record those so I could then have SSH working again, so I can remotely check on my machines.
While that is easier to do remotely, most of the time I want to check on it, I am in my place, and it is as simple as turning on my TV and switching input settings to the appropriate computer. (If that's not just as easy (if not easier) as going in the terminal and entering commands and passwords, I do not know what is).