Pools can certainly be a lot of work. Yesterday I had a bunch of needles in my 3 way Jandy Valve. 
And then I had more in my pump basket. A couple of years ago I retiled and did an epoxy process on my pool. Oddly enough I almost never test my pool anymore. I got used to knowing what it needs and being able to just wing it with the chemicals and it looks good.
Update: I also do all my own pool repairs. It cost so much to have other people work on the pool.
I fix the pipes and retiled and recoated the pool.
Just saw your updates, damn that's impressive.
I want to gut all the equipment and move it to the pool shed rather than by the side of the house with our central air. It's an eye sore and wasn't done well. I also want to add a stenner pump to automate the liquid chlorine
My equipment is in a bad spot as well. I'm not sure if it was because they couldn't place it further back because the pressure would be greater getting to the spa or what. The pump basically runs both the spa and the pool and I'm able to switch it to either one by rotating two jandy valves. My equipment is from 1990 but I keep bandaid fixing it all the time and it keeps going.
I can mostly manage on a daily basis without testing as well. I will test chlorine every few days to correct any estimation errors but I rarely measure how much I pour in and just go by gut feeling.
On a larger pool, there is a lot of wiggle room.
It looks like you have a lot of trees around so I'm sure when there are storms that makes it a lot tougher. Here in Arizona we don't have rain coming down right now so it is a lot easier to control. My biggest problem recently was a lot of pollen coming off a tree in the neighbors yard which threw some stuff off.
Once monsoons hits I have to be on it a little better because the rain will throw the chemicals off.
Trees can be a pain, mostly at the end of the season.