I have a very similar issue with the exact same boat. For me, it is the relays. The relays are the two black (1 inch squared) boxes on the left side of the trim motor. You can pull them straight up and out just like you would a plug into a wall outlet. I replaced my relays at one point with relays I bought at Auto Zone, but realized this wasn't the issue. If I squeezed, tapped, or "Fonzi-ed" the relay while someone was holding the button, it would work. Ultimately, I discovered that the female side of the relay connection was too loose to keep contact with the relay. That being the case, I used a small screw driver to push them tighter. I just did this last Friday and the trim worked all weekend. I hope it continues to work over the holiday weekend. You could also try to clean the contacts on the relays which I did by spraying them with WD40.
My trim indicator also does not work. Mine is because the wire is cut on the sending unit (which is located on the right side of the out-drive), but yours could be the result of the dreaded VDO cluster (if you have it). Search for VDO cluster and you will find plenty of threads about that.
Good luck and let me know if you have any further questions.
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2001 Four Winns 180 Horizon
4.3L Volvo Penta
