My trick to winding the Speedy Pro was to sell the Speedy Pro and buy the FOIS -- problem solved!
It definitely gets easier with time and regular winding. I also picked up a few "winding tools" which helped but were a bit cumbersome. With any of the Speedies the winding is an integral part of ownership, and I appreciate the ritual and the flexibility that comes with daily winding, since it assures that I'll always have a watch ready to wear.
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