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I'm finally putting together the MRS on this older 26D. Roger used an S hook in to the center mounted forward cleat to attach the pulley system going back to the gyn pole. That is fine except that I have not used that cleat for anything in the time I've owned the boat. Has somebody been using the original mast raising system in this way for awhile? Is that cleat backed well enough to support the almost straight up pull without stressing the deck over time?

Also, do the plastic cleats that were originally used hold up in the sunlight, or should I just replace it before I even start to attach the MRS to it.

Would it, perhaps, be a better idea to make the gyn pole longer and attach it to the headstay fitting, where the Jib would be attached after the mast is up, or is the extra work not necessary?

If you attach the bottom block or static line to the forestay chain plate, you won't be able to use the MRS to pull the mast forward while you pin the forestay. I would attach it somewhere else.

I have a 26D and the factory MRS, and I always attached the lower block of the MRS to the Jib attachment point on the head stay attachment fitting. It works fine without making the pole any longer. I use the jib sheet to pull the MRS pole as high up at an angle as possible, so its not at a 90 degree corner with the mast. That little extra height makes it work. I use a shackle as I just don't trust S hooks. When I have the mast raised I attach the head stay to the upper hole in the head stay fitting.

I agree with Mike that the cleat can be used. Our 1990 S uses the same cleat. I think it’s nylon and tough. I see no sign of fatigue on the deck. The real load is not that huge and only pulls heavy for the first half of the lift. If you are concerned have a friend assist, by actually lifting on the mast for a lift or two until you gain confidence.
Definitely trade out the ‘s’ hooks as suggested.