Whenever I plug something to an outdoor outlet, it shorts out the water pump and I have to hit the reset button on the pump to get it going again. Even a small iPhone charger in the outlet will trigger the short. No breaker is tripped so I am guessing its a loose wire or ground that is tripping the GFCI.

When I had the electronic gate opener installed, the installers seems to have daisy chained off this outdoor outlet as there is a white pvc pipe directly under the outlet going to the gate opener.

I never used the outdoor outlet and noticed it the other day. Does Homepro do a good job at diagnosing these type of issues and fixing them?

you could start with basic trouble shooting

goto your house CU, turn off all breakers, then have some one watch at the pump as you switch them all on, one by one.

When you have found the breaker that turns on the pump. Switch all other breakers to off again, but leave the breaker for the pump on.

Now plug the charger in the outlet that you say has a problem, then see if it resets the pump. If that is the case, the electrician that wired your house has put all outside outlets on the same breaker. Also see if your electric gate is still working then.

Also see what happens if you plug your pump into that specific outlet and see what it is doing.

You could ask HomePro to fix it for you, but they will only help if you bought the pump there and it's an installation failure, if not expect to pay a substantial amount for them to come over and fix it. Best bet, and cheaper would be to find a local electrician and they can diagnose the problem further or you can ask the gate installer for help and tell them of the problem, other solution is of course stop using that specific outlet 😉