Yes, good stuff for coax connector sealing.I use self fusing silicone tape and leaves no residue either but like above it is tricky in a tight spot.
I'll keep your idea in the memory banks though
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Looking at you pic again, it seems the rubber hose washer would act like a rain shield and let water drip away from the connection point which should work fine for that.Take an ordinary water hose washer and slide it onto your SO239. You’ll find it is a perfect snug fit.
Then simply screw on your PL259. Bingo! No more sticky coax seal, etc.
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Multiple washers is an idea I tried. Quite frankly, a single one placed low on the connector works good as the washer is pushed upward as you screw on the PL259. Mine did not deform at all.Looking at you pic again, it seems the rubber hose washer would act like a rain shield and let water drip away from the connection point which should work fine for that.
To add to your idea, I think putting a couple more washers on the threads so the connector will bottom out all the washers and create a tighter seal at the edge of the connector.
Just be sure not to use too many washers where tightening the connector will deform the rubber washers.