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Eddie,

I would think that a watch winder is going to only give it the winding power that you have set..and it will vary... If you put an already well wound watch on the winder, it will keep it there for quite some time..

If it is not wound at all, then it will wind it to a point, and it will tend to stay at that point as long as the winder is working......it could be to the point of clutch slippage since that is the watches safety feature, after, if the rotor is turning, it is trying to wind the watch... however, most winders are designed to just keep it running until needed...

As to wearing vs. letting it sit either in a winder or on a desk.... a worn watch will usually run faster than one that just sits.........The movement of your wrist and activities tend to change positions and amplitude of the hairspring off optimum so it gets a lot fewer full amplitude swings than it would just sitting....therefore, it will gain a few fractions of a second..