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1952 Chrysler Windsor deluxe question

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Finally took my newly acquired Windsor on a longer journey (100 miles round trip). Drove for about 45 mins on the freeway then got off and stopped at a red light. I started in LOW from the light and the car wouldn't shift into the next gear and I skipped and went into DRIVE. when I heard it clunk like it shifted then it shifted again, had to skip second the rest of the way and go straight into drive. The questions I'm asking is what could be causing this as it only did it when the car had warmed up. The second question is should I even be starting in low, the previous owner said to start in low and then go into drive. I cant even get the thing to move in drive from a dead stop without it wanting to die. Were also struggling to find front shocks for the car. 

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