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The parts came in the mail Yesterday. I realized very quickly that it would be impossible to install the roll pin from above with the gearcase bolted on just as everyone had said. Took the gearcase off and followed the recommendations from Mumbles. With everything having been freshly cleaned and put together, the job did only take about 15 Minutes. Using the 2 by 4 as a support was key.
On a side note, with the parts, finally, I got the correct tiller gear/shaft for a 1955 Fleetwin. It is the one with the squared off gear teeth and came from a 1954 Fleetwin. Also, put the tiller assembly back together again, and it works well. It’s a great feeling to get going again after my project got stalled for a while. Thanks to all!
Improvise-Adapt-Overcome