Lots of structural engineers tend to go overboard with the structural, they don't want failures and they aren't footing the bill on all the extra rebar and concrete. Speaking as a contractor, not a pool contractor, it is a sliding scale, mine's pretty flat until I start going through gates by the country club or worse, guard towers! It seems funny to me that I first check in at a guard tower, drive through the gate into the subdivision of expensive houses to drive through another gate at the property. How bad are your millionaire neighbors you need a gate at the end of your driveway to keep them and their spawn off your property? Getting multiple bids is important, and vetting them from references is cheap insurance. I prefer working with smaller more personal companies myself.