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Thanks everyone for the tips and suggestions. I honestly don't think I cracked anything because I really never cranked it down. My only concern is if I got the leak to stop with the last tightening using the torque wrench but lost some rubber from the O ring. Should I still think about draining oil and replacing ring?
I would because it would bug the crap out of me, but **** issues aside, I would just keep am eye on it. Not like it's going to pour out if the o-ring fails more. Keep a new o-ring on hand just on case and be ready to deal with it.
This is such an easy problem to fix. Go to Lowes or Home Depot and go back to the plumbing department where you can buy about a dozen or so #41 O-rings for a couple of bucks.
I rarely replace the O ring. I put a dab of thread sealant on the threads and hand tighten it with a wrench. When I remove the plug I clean the threads real good.....easy peasy.....nuff said.