re: raising
Rob, I've got the same 85 h23. I don't think it is possible to raise that mast with less than two people and I prefer three. When deciding on how you want to raise the mast, I'd consider how often you'll need to do it. If you are a trailer sailor and will be raising and lowering the mast often I'd invest the time and money in designing a system. If you are like me and only need to raise the pole once or twice a season I'd say get a pair of friends and a 2x4 to help. I don't use the winch either. I once tried walking up the mast while my wife helped with the jib winch and found that the load was too much. Now, I use the mainsheet blocks to raise the mast. I attach the single block (normally attached to the boom) to the shackle of the jib halyard and the block with the cam cleat to the D-shackle in the anchor well (that normally attaches to the jib tack. This way I get 4:1 purchase and lifting is slow but easy and the person who walks the mast up does little more than make sure the mast does not sway on the way up. I have a third person hold an 8 ft 2x4 with a small v-notch cut in the top. One end of the 2x4 rests on the deck immediately in front of the mast base and the 2x4 is angled forward about 70 degrees so that the jib halyard runs through the v-notch as the line is tensioned while raising. Its not pretty but its simple, cheap and works. (Of course make sure the other end of the jib halyard is secured to the cleat on the mast)