My opinion, it looks like you should have used a little more resin. From the pictures of the outside of the transom you look to have some dry edges and once you wet it out it should have had a clear appearance unless I am missing something.
The wood replacement looks tight. You should definitely glass over the top of the transom as resin alone will crack and allow moisture to get to the core. What year is your 20? and how did you remedy the stringer rot?
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