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1980 240DD Transmission Rough at Start

I have a 1980 240D sedan with an automatic transmission. When I start the car and drive it first thing in the morning, the transmission shift from first to second gear is rough, it snaps my head when it shifts! However, once I have been driving it for about 15- 20 minutes and it's warmed up, the shifting from first to second is much smoother and about the same for the other gears. Is my transmission having a problem, or is this typical for a car of this age?

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1981 300SD Low compression #1 cylinder

I finally got around to checking my compression and found (the car has 300K+ miles on it) all cylinders had 280-325 on the compression EXCEPT #1 which I checked 6 times with different crush washers and could never get over 160.

I'm thinking I need to recheck my valve clearances one more time. What else can I look for to try and figure the problem?

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