We’ve had our 1987 Legend 37 for just over a year and love the boat. Our family enjoys everything from lunch onboard to an afternoon cruise to swimming in the lake to a quiet sail. Although we haven’t raced as much this past year, it has proven very capable on the race course. Our Mackinac crew eas impressed with the stability and control during multiple storms. In short, I think it’s a great boat.
Ours is the deep draft keel, but there was a wing keel in our class on Mac, and seemed equally capable in all conditions as well.
My understanding from shopping for a Legend 35 or 37 (we would have considered either), was that water in the deck, especially near the furling-line thru deck, is the major concern with these boats. The second big area is water in the rudder. Extensive discussion can be found in these forum on both issues. We actually found on this forum that our rudder had been rebuilt several owners back, so never know what you’ll find in the archives!
Third issue is water leaks from the deck port lights… we need to rebed ours…
As for the your plan, don’t underestimate how expensively will be. A mast unstep, haul-out and transport will be, even local, into the thousands… and no use during that time. And the same costs when you’re all done with the retro and want to get it back into the water.
I’d encourage to either look at adding those costs to your initial purchase budget, or use them to pay someone to do the essential work, which will get you enjoying the boat sooner.
It depends on what you want, a project in your backyard or to go sailing. It’s your choice of course, but I’d at least double your expectation on how long you think the retrofit will take you… do you want a boat in your backyard that long? And really quote-out the yard fees for hauling and transport fees, and consider if you should spend that money on a different boat or on paid labor.