Sounds to me like this guy did a bad installation. If he did what I think he did, the drip edge is BEHIND the gutters - hence not serving any purpose.
Nailing into the fascia through the gutters has always p***ed me off. Previous owner had someone install 14 guage full apron galvanized gutters that were double lapped at the seams and they STILL nailed into the fascia - resulting in water rotting them out in a couple of years.
Only way you can get at those nails without ripping the shingles is to put a crowbar tip on the nail and hammer on the crowbar a few inches back.
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