My advice is to cut the skin see my post very important where you cut it, I ran into the same problem solid wood at the bottom, Nothing beats removing all the wood this is very important since the new transom will be much stronger by gluing it self to the bottom of the Boat this is its strongest point of contact.
Its no big deal attaching the skin see my post if I can do so can you.
I use Resin (Gel) from Auto Zone and mat& resin from Boaters World
The time and effort you save by removing the skin is worth it.
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