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The the 1954 and 1955 Fleetwins are always hard to pull over when cold. They have a relatively small simplex starter pully. In 1956 OMC introduced the larger eas-a matic starter with a cam design on the Fleetwin that made starting much easier.
The fact that the motor is still hard to pull over with the sparkplugs out, makes it sound as though there may be a sprung or broken pinion shock. To determine this, the upper bearing and seal housing must be removed. If the bottom of the upper bearing is somewhat mashed, then the shock may be elongated and making contact with the bottom of the bearing.
Remove the pinion shock, and get a good measurement of the length. It should measure exactly 6-11/16″ long. Any longer, and the shock is sprung or broken. I just removed a broken shock that was 6-13/16″. After a good cleaning, and a look inside with a high intensity flashlight, a 1/8″ separation in the broken spring could be seen.
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