For the ongoing/routine items, I'm less sure - though have a pretty good idea of some routine stuff, like lawn mowing, other things feel like a complete guess, like how many plumbing calls will I'll need per year per unit? 

Generally any hold of more than a year is considered routinely safe.

Personally, I would create a routine around the test taking experience.

Although having to inspect beautiful beaches across the world is part of my investing routine.

What is everyone using to track their daily routines, or tasks, etc.

If you're going the umbrella insurance route, perhaps see if it will cover you for several things including just the routine slip and fall (like mold or earthquake).

Over at her place with the HVAC tech doing routine twice a year cleaning maintenance on her unit. 

Build routines (no different than dieting, working out, etc.)5.

My routine, 1-2 hour breakfast/coffee with my buddy.

Most people are happiest with a daily routine surrounded by intelligent peers doing something both gratifying and remunerative.