Wow...you guys are awesome! Sorry I didn't get back to you until now...work got in the way.

Let's see if I can answer all the questions here (forgive the explanations...I am definitely not an electrician):
1) The circuit breaker is labeled 20amp "dual pole?" breaker. Sorry, I don't know the specific name for it, but it has two circuits that are tied together...since there are two maybe that makes it a 40amp? It looks like this picture, except with some white one it which they tell me is the GFCI-specific part.
http://www.aaronssupply.com/file/2014/08/06/Siemens_MP220_20_Amp_Double_Pole_Circuit_Breaker_1.jpg
2) Our county code requires GFCI on the pump. The PB thinks its a "stupid code" and I have no knowledge to disagree or agree with them...but they are trying to stay "legal", which I appreciate.
3) I have not been able to recreate the tripping while I am there. Generally here is what happens. I wake up, notice the pump is not on or come home and notice "****" on the water surface and pretty much know something is wrong. I spent an hour last weekend spraying a hose on the equipment like "rain" and could not recreate the problem to make it trip. At first I thought it was happening only during/after a rain, but this week it tripped without any rain or sprinkler or any water happening.
4) The ozonator is on the same circuit as the pump. They had the ozonator checked and they plugged a hole which they said it problematic during rains as water seeps in. Unfortunately it is hardwired into the circuit and has no "on/off" switch so I can't eliminate for troubleshooting purposes on my own. Also, it is "always on"...I assume...since it isn't on a timer. My assumption it also that it also is only "live" when it the pump is scheduled to run.
5) No commonality on day it trips. Sometimes its during the week, sometimes on the weekend.
6) Speaking with the PB, they did replace the seals and something else in the motor, unfortunately that has not helped. What is "meggar"ing?
7) This breaker is in the Zodiac/Jandy RS-8 control panel. Not my main home control panel. The Zodiac panel is on the other side of the house by the equipment and they ran conduit through the attic to the main house box on the other side. I'm guessing since nothing else in the Zodiac box trips, this is not an issue with my main house electrical...but again, certainly not qualified/certified/licensed.
8) I do have another GFCI outlet on the outside of the Zodiac box. Nothing is hooked to it (my landscape lighting is hardwired to the relay), but I never have to hit the "reset" on it after the breaker trips, so I assume that is not the cause.
9) The electrical company they sent out replaced the breaker once...but again, with a GFCI one, not a standard one.
Thanks again for the questions...let me know if what I have provided makes anything "trigger" or if you guys have any other questions. The PB is about ready to send out a Pentair rep to check it out...so they are trying...which is nice to see.