well i had cut a transom down like the guy did on your boat and we thought it looked better and were saving money by buying a short shaft motor. (we were cluesless idiots about boats and motors obviously lol) it cost me $300 to get it properly resealed in fiberglass again but that was 15 years ago.
fiberglass is easy to do but not always easy to do it right so it doesnt crack or split over time. the point is i wouldnt think having it sealed properly by someone who knows how to do fiberglass correctly or even getting it returned to its original designed shape and height shouldnt be super expensive thing to do. if it is sealed properly a jack plate can be used to mount a long shaft motor to it and have the cav plate at the correct level.
only you know the condition of the boat and motor well enough to choose the path to take
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