Walk all over the floor on the balls of your feet, kinda bouncing as you go, feeling for any area that feels soft under you feet. Raise the engine and push down on it from outside, looking for any major flex in the transom. Look at the transom from outside, look at any holes that have been drilled into it. Were they sealed with something or just left open?
If they are not sealed, take a very small drill bit and push it into the holes, then pull it out. Look at the wood chips (if any) that come out with the bit. Are they like oatmeal or are they like wood? (Oatmeal usually means some rot is in the transom)
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1987 V20 w/1987 150HP Yamaha on a Shoreland'r Trailer
1978 16.5 Airslot w/1996 120HP Force on a Four Winns trailer
1996 V21 w/1993 200HP Mercury on a Shoreline Trailer
All towed by a 5.7L Hemi Durango.
If God didn't have a purpose for us we wouldn't be here, so
Live simply, Love generously, Care deeply, Speak kindly.
(Leave the rest to God) 
Silence, in the face of evil, is itself evil. Not to speak is to speak, not to act is to act. God will not hold us guiltless.
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