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I have a 1952 F-1 with flathead and column shift.When I start off since it has got colder before the truck warms up second gear is stiff and hard to shift into.Sometimes I just go to third and skip it.After things have warmed up every thing shifts real smooth.Is there anything I can do for this?
I'd check the clutch adjustment first, mine was doing similar and I just had too much slop. It could also just be that the synchro is worn, and when the oil is cold, it isn't spinning freely.
If Ross's replay doesn't cure it, maybe synthetic gear lube will help. It lubes as well as dino oil, but stays thin when cold. I've noticed better cold weather shifting on my cars after switching. It's available in 80/90w at most parts stores.
I'm with rhopper, likely 50 year old gummy tranny oil is the culprit. You will probably need to drain and refill it after a 1000 miles a couple times with syhthetic to clean out the old gunk.