Greg,

I forgot what kind of boat you have, but if I remember correctly it's a Narca. So, what I do may not work exactly for you, but I think it wil help steer you in a more simple direction.

My fore mast support on my trailer is 60" high and mounts to the trailer tounge. I have a Trailex so I ordered the long mast support. I did this initially so I could car top my kayaks and bikes while towing the boat using it for a mast stepping system was a bonus. Anyway, at the top of the mast support, mount a sheave (an old winch drum works great) and mount teh boat winch below it at a convenient height. If you are tall, you can mount the winch up high, but it doesn't work well for dragging the boat onto the trailer that high. Basically, you want the sheave at least 24" above the mast step so it is effective. The higher the better. If I am alone, I use a step ladder to support the top of my mast. The ladder fits nicely under the boat on the trailer. If I have someone with me one of us holds the mast above our heads while the other cranks it up. I use a set of trap wire to steady the mast when it is at a low angle. I tie the off to the front cross bar. After about 45 deg the shrouds can take over.

I try to keep it a simple as possible and use components that can be used for other things as well (like a winch to step the mast and drag the boat onto the trailer).

I have seen lots of fancy systems to step masts out there. Most are too complex and too $$$ to be worthwhile.

I hope this helped somewhat.