Update:
Thoroughly cleaned the breather plate, reed, and hole. Replaced the filter media in the breather housing. New gaskets are installed on the breather and carburetor. Purchased a couple o-rings from the hardware store and stacked them on the dipstick. The dipstick now seats tight like it should. I ran the tractor for 10-15 minutes and watched both the dipstick and the breather. The dipstick no longer pops out during startup/shutdown and the breather no longer leaks oil nor does the dipstick hole. Everything is behaving as it should.
Thank you for all the help!!!
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