Had the same problem with my Yamaha SHO. Took it to Rockwall Marine ( it ain't as easy as you might think ) and had them fix it. They also had to replace the boot where it connects to the transom. Total cost, parts and labor
$140. Saved me all the stress and headaches. Those guys are good and honest as the day is long.
Long ago when men cursed and beat the ground with sticks it was called witchcraft, nowadays it's called golf.