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Cutter Rigs Vs. Sloop Rigs
Larry, as much as I hate to say this, you are really fighting an uphill battle. There are a lot of factors that control how well a boat goes to windward. The sail plan is but a very small part of the problem. Going up wind you tax a boat''s stability,foils and hullshape.
It works like this. To really get good windward performance you need a higher aspect ratio rig (taller rather than longer). High aspect ratio rigs generate more drive with less drag. This would mean increasing mast height and increasing main and jib luff length without changing the horizontal dimensions of the rig.
For this to yield much of an improvement you will need better sails. Mac''s original sails are really junky- stretchy and not very well shaped.
Then there is angle of attack. With the new taller rig lead angle will become the problem. To improve this you would need to add inboard jib tracks and shrouds, and a high quality traveler and vang.
Of course none of that will help much is you don''t imporve the foils and stability. The taller rig will make the boat want to heel more. The standard rig is designed to feel stabile by not over-canvassing the boats limited stability. With the taller rig and greater sail area you will heel more and so make greater leeway negating any gains that you made in your sail plan.
Then there are the foils, keel and rudder. These are proportioned to your smaller rig size and to the limitations of the hull shape and rig. A new keel and rudder would be necessary to get better windward performance. The keel would probably want to be lead which would increase stability over your current glass and iron board. Of course then you will need to beef up the structure and lifting equipment to handle the greater weight and loadings of the heavier centerboard.
When you get done with all of that you will have a boat will still be limited in its pointing ability by its hull form. That said, if you did most of the above, pointing ability would improve.
When all is said and done, new sails would probably make the biggest difference but unless you did the whol program you would never achieve a boat that truely goes to windward very well. With all due respect, if you really want a boat that sails well on all points at a reasonable price you would be far ahead to change boats. Using any kind of objective analysis, there is no way it would ever make sense to put that kind of money into making your Macgregor a better sailer. There are really better built and better sailing boats out there for the money and frankly, if you care about how well your boat sails that would be a better way to go.
Respectfully
Jeff
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