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I wouldn't use bondo by itself along the edges as it chips easily and can break off. Fiberglass resin would be better, then foam weather striping and possibly spray foam on the inside to make it form fitting. I don't think you can make it totally leak free.
As far as making it easy to put on and off try this.
Take a roll around floor jack and remove the steel pad that you lift with . There will be a hole where the pad was. Weld a similar size pin to your hitch. Place hitch pin in the hole, lift to put on or off. Use the pressure of the jack to help align top hole bolts.
It should be a one man operation.
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