Me too

OK, the trim kinda works so I suspect that the contacts inside of the switch are worn or dirty and you are losing contact when you go back down a little. You might try taking it apart and cleaning, maybe bend the copper wiper a little to increase contact. If you do make sure you mark everything. For the trailer switch, sounds like a contact problem, but as you say makes no sense. Time to get out the voltmeter. In the stern there are two black wires from the trim limit that go into two connectors. One with a purple white/wire and one with two blue wires. The P/W wire comes from the trim, and passes through the TL switch. One B wire is from the trailer switch and the other B wire goes to the up trim pump relay. You can unplug the black wires and with the voltmeter see if you get 12V at the blue wires when you hit the T button. Try cleaning up the contacts there and at the relay. Just a guess. When you figure it out let us know what it is.