I know this is a revival of a revival, but I'd love to see pics of 1 and 2. A gin-pole/A-frame/ angle-improver setup is relatively easy to work out. My problem is how to slide a 31ft mast out past the rear crossbeam and support it with it turned 90 degrees to get it onto the ball and then limit the mast turning back straight until the downhaul is clear as it's lifted with a winch/gin-pole arrangement.
As for limiting the mast from the 90 degree position:
I have a non-stretch line on a the winch which goes through a block setup up at the top of the mast support on the trailer. The height is just right for leveraging the mast once it's on the ball and raised about a foot or two off the rear crossbeam. I attach the line around the mast above the spreader and tie it back onto itself with a trucker's loop(I make the loop point the same as the forstay end length to allow me to untie once the mast is up). This keeps the mast at 90 degrees when raising.
For side to side control I use my jib blocks with cleats clipped to two eyelets on my trailer cross member on either side of the front crossbeam. The jib sheet is then attached to a trap wire per side.
So from one position I can crank the winch, raisng the mast and steady the side to side motion with the jib sheet.
There's room for improvement but since I only set this up once or twice per season it works for me.
Tim