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Hard starting cranks won't start. on 2001 Ford F-250 Super Duty

I really have 2 questions, first, I keep it plugged in during the cold weather, it cranks good, won't start, batteries check good. Finally a little jump and it starts.

2nd on a small or medium incline automatic transmission doesn't engage fine and smooth all other times,

Asked by for the 2001 Ford F-250 Super Duty
YOUR BATTERIES MIGHT BE GOING BAD INTERNALLY AND SULFATING. ON YOUR TRANS ISSUE HOW IS THE FLUID LEVEL AND COLOR. YOU MIGHT BE HAVING A CONVERTER DRAIN ISSUE. CONVERTER MIGHT BE LETTING FLUID DRAIN OUT AND THIS TAKES A FEW SECONDS TO REFILL AFTER START UP.
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