Hey Mike, I just popped in and saw Cypress in your title, so I had to skim over your thread! I love your design!!! The lines are great!
I think you may have found the answer to your question regarding draining the pool, but I'll add how it works on my pool.
When Harvey hit, there was no way my overflow drain (the small grated one just under the coping or lip of the pool) could keep up with those rains.
My pool does not drain to the sewers but to the street. Luckily a member from Australia was awake and on TFP at 2:00 in the morning to tell us what to do before the water came into the house. We hooked up garden hoses to the spigots at each pump (3), opened the spigots, and drug the hoses around the garage to drain down the driveway (and not into neighbors' yards). It saved us. I think that probably worked faster than a sump pump would have. Anyway it worked for us for the duration of the hurricane. TFP saved us, because I had no idea I could hook up my hoses at the pumps to drain the pool faster.
So you had the Big Dig!!! I remember how exciting that day was!!! You have many other big construction milestones to look forward to! I jumped around like a little kid with each one!
Enjoy and take care,
Suz
PS. Awesome video! The crew was much neater with your dig than the crew for my did! Fun music, too!