Try the trailer button from any drive position. It it goes up
Bt Doctur is pointing you to the problem. The trim limit switch is misadjusted, failed, etc. To check adjustment, loosen the two clamp screws on the trim limit switch hsg. (port/left on the gimbal ring), rotate it slightly clockwise. Pay attention to the position marks so you know where you are. This should allow the 'Up/Out' button to raise the O/D earlier. Correct adjustment is shown in the attachment. If there is no change by rotating the limit switch, it is either bad, or disconnected.
Locate the trim position/limit wires inside the transom plate. (see attachment, 'd'). The trim limit wire has two wire connectors. If disconnected, reconnect to the engine harness- they are male/female- and try again. If no fix, time to replace that sensor switch. This is painful since you have to pull the O/D, and remove the bell hsg. pivot pins. Instructions are in the Sierra kit. You will need a special socket adapter to remove the bell hsg. pivot pins, and a pivoting 7/16 Gear Wrench ratcheting box end wrench. Change both Trim position and limit switches while you are this deep in the situation.
Or you can jump the two trim limit leads in the engine harness. This takes the limit switch out of the circuit. But CAUTION!. That switch is there to prevent prop cavitation at too high a trim setting. More important, it protects your O/D's cardan U joints and gimbal brg. from over stress that occurs when torque is applied at a severe trim angle.
I cringe when I see some hoople head doing full throttle, full turn donuts. Unnecessary abuse to the out drive.
