You are mowing in one of the worst conditions possible and when a blade hits a correct object the blade momentarily stops and loosens the cap screw never to be tightened unless you stop and tighten it. If the cap screw looks anything but pristine condition I would replace it.
Sorry but you really need to think this one through, draw it out on a piece of paper if you need to.
All mower decks are designed to self tighten in use so the bolts can not loosen when the blade momentarily stops
The blade may stop but the spindle does not so the bolt gets tighter
However the blade can spin inside the cups that hold it to the spindle and deform or wear a shallow groove , just enough for the blade to go a little loose .
Back to Rosco
First as a municipal authority you should be able to get them ( and all your parts ) directly from GrassHopper at trade price.
Also because you are a municipal authority you should be able to get swing back blades.
I know that Walker do swing backs, I am about to replace a set this week
Next have a good look at the cup washers, they have probably gone flat & are no longer doing their job of holding the blades tight under spring pressure .
Your diagnosis is probably correct, they are getting over tightened and are necking, so some Blue locktite as Mark suggested might be the answer and be careful not to overtighten them from the start