Anthony, The reason I like to check the oil when it's cold, is simply because I know all the oil is definitely all down in the pan. You are right if one is checking the oil when it's hot, you should wait about 10 mins. I don't know if the oil level reading on the dipstick is different when hot versus cold. The only explaination I can think of for my situation is maybe the dipstick doesn't go straight down into the pan. It may go in at the bottom at such an angle that the oil reads higher on one side versus the other. That is why I was thinking that I should take the average between sides. I was wondering if anyone here knew for sure.

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1999 MB SL500 (110,000 mi)
2004 Volvo V70 2.5T (220,000 mi)
2014 Tesla Model S 85 (136,000 mi)
MBCA member