You'll always feel resistance as you wind it, it needs to be wound until the crown can't be turned any further. At that point, it's wound fully. Some people feel resistance and stop winding for fear of breaking something, and then wonder why it stops after 15 or so hours.
Some Speedmasters are harder to wind when new than others for various reasons. They will loosen up with wear, but if you pull the crown out and put ONE small drop of oil on the tube that will immediately help.
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