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Enclosing the transom is possible and costly. I was interested in pursuing that on my 1992 outrage 19 I. I talked to several fiberglass guys and several high end boat builders. All advised me not to modify the hull. If your serious, I would do the same and consult with your local fiberglass guys and any high end boat builders. I would think the easy thing to do would be to repair the transom if needed to accommodate a single motor. If considering twin motors, a pair of used or new suzuki 140's could be a good option (cheaper and less weight). Do you need jack plates....? The less you need to modify the better.......my opinion...