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Drill a small hole on the inside of the transom, in the bilge area, and check the wood shavings to check the color and if it's wet.
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My transom doesnt go all the way down to the bilge. it stops 8 inches higher in a fiberglass ledge.I cant figure out why the back will not suck down. ive tried with ratchet straps but cant get it. I might cut it open and just do it all. I know the wood is wet for the top 6 inches at least.
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If the wood is wet it definitely needs to be done. Good luck and check out youtube for vids if you are going to do it yourself and ask these guys on the boards. They are full of information.