I've had a little experience with things similar to your rubber ring. Fighting them is frustrating, I agree.
Rather than trying to fix it from the top side down, try inserting the rubber from the under side of the hole and pull it through to the top. That upper part will pass around the metal hole and then the rubber slot will fix around the metal.
Also, squirt the rubber with dish washing liquid and get it REAL slippery. Then use a pair of pliers (so YOU can grip it). Gently pull it UP through the hole. After it's inserted, rinse the dishwashing liquid off.
Good luck.
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2019 Montana High Country 375FL
2014 Chevy Silverado Duramax, 6.6L Dually
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