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Welcome to WhalerCentral. I am from South Portland but currently reside in KY.

#2/3

It reads as if the motor is mounted all the down and resting on the transom. I would also guess the bottom set of bolts are through the blind holes or lags.

Motors installed prior to 2000's tended to be put on too low by mechanics and dealers.

To solve #2 and also help with #3, I would suggest you review the engine mounting articles in the reference section:

http://www.whalercentral.com/articles...cle_id=106

http://www.whalercentral.com/articles...icle_id=82

I would hold off on the prop till you review the engine mounting issue.