"Am I just being a pansy and I need to just keep chipping away at it?"
Your not. Do your drill extensions reach the entire depth of the transom? If so, don't force them, let them do the work. Drill as much as you can in an area then use "whatever means possible" to loosen the wood chips/fibers. It will take some time. The flat blade I used acted like an ax and I was able to get the wood out in little slivers. Not efficient, but it worked. I had some sore arms when it was all over but I bottemed out on fiberglass across the entire width of transom.
Maury
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FLOUNDER
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