Mike-
I don't know what your tilt trailer looks like or works like but back when the 18squares were using tilt trailers that was the easiet I ever raised a 31' mast! Process consisted of hooking up (or leaving hooked up) the "upper" side shroud (ie the one to the raised hull), sliding the mast back- cradled in the rear mast holder- putting mast base on the ball (NACRA system- mast had to be turned 90 degrees- but since it's to be supported by one side stay pointing mast "up" was way to go anyway!) then simply swinging mast forward (also swings slightly up- it's rotating around an axis between the mast base and side shroud), hook up forestays and "lower" side stay and THEN "detilting" the boat to flat. Dropping mast is reverse. It does put a little more strain on the tilting mechanism, but if it can't handle those loads fully tilted you are probably in trouble anyway!
Hope this helps-

Kirt