Re: Is this a sign of transom problems?.
You can drill into the transom from the inside. Small 1/4 holes. Start at the bottom and work your way to the top.
If you get clean wood great!! if you get dark dry wood its not to bad, if you get dirt out ther hole you have junk!!
Should have the worse near the bottom and get better as you go up.
After you do your ck, fill all holes with some 5200 or other caulking!!
If its all dark like you say but wood you should be ok for a long time!! Just make sure that what ever is bolted o going to be bolted is sealed with 5200 to stop any water from getting in!
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1986 V20 
Old Fishermen never die, we just SMELL that way!!
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