Hi Sratz Welcome to this site. Tile the motor to the up position, then push down on the end while looking at the transom.... if it flexes you will need to look further... Also, take a hard plastic handled screwdriver and tap all over the transome from the outside... you should hear a sharp tap... a dull, hollow sound is another sign that you need to look further...
Finally, in order for any of us to help you like they say, a picture is worth a thousand words... 
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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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