I have a small O'day 19 for which I drop the mast. The principals should be the same here though. I use an electric winch that is mounted in the bed of the truck, which makes it need two people, but if you set up a winch system on your boat that should work as well. I also used to have a Chrysler 26 which I used one of the winches on the boat. The gin pole is important to make it so that you can fully lower the mast without losing leverage. The side stays will not help you keep the mast from swaying sideways as they loosen as you lower the mast. What is needed is a bridle. The bridal must have a center point that is at the same height as the pivot pin at the bottom of the mast. It must also be the same distance between the front and back of the boat. To do this you need an upside down 'Y' of low stretch line or cable that connects to the foot rails of the boat such that when it is pulled up by a halyard that the junction of the 'Y' is exactly at the point described above. Then when you lower the mast it should keep it from going from side to side. In my system, I have metal 'O' rings as that junction point. I use the halyard to pull both sides up together connecting both ends that get raised with another "O' ring. The challenge is to get the bridle tight enough. So if you can build some sort of leverage into the system to pull it very tight, yet be able to loosen it to get it undone that would be important on a longer mast like yours. If you can use cables it is much better than rope, but then you might not be able to set up the system with the mast already raised if you don't use a halyard. I agree with others that you need to be able to stop part way and check all lines for anything catching on a cleat or what ever. Good luck.... and get one other assistant if you can. Don't rely on the stays to keep it from swaying off in one direction or the other.