With the motor out it easy to inspect the pan for heavy rust, starter cobnditon , motor mount condition etc,.and if not done in 5-8 years the rear motor mount bushings especially from the impact shock on the motor
Had a customer who has been there, replace the transom housing because there is unseen damage and you most likely lost the seal and will take on water .
Could be the trim pump up pressure is low. Try reversing the lines at the pump to see if it will raise with the lower pressure of the down side. Just remember to switch the lines back
