Welcome to the site.
You can drill a few small (1/4) holes on the inside of transom and see what comes out? Clean wood you are great, dirt you rotted.
You can also just put the motor on there and when tilted up, grab the tail of the motor and lift up, cracking or movement you need transom, n cracking sound or movement you good to go.
Can also get a Jack Plate to lift motor up the 5" so you are able to run the 25" shaft with out filling the transom. If the transom is in good shape.
Gas tanks are 20 gal each.
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1986 V20 
Old Fishermen never die, we just SMELL that way!!
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