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I have done this. You may need to be able to move the boat forward and back a bit on the trailer to position it correctly. I removed the rearmost roller that us under the centerboard (the boat still should be supported by the carpeted supports at that time.) The front of the centerboard well should be 4-6 or so inches behind the next roller forward. Being able to drop the CB those few inches at the rear of the well should allow you to drop the CB at the front of the well even further (the rearmost edge of the CB can go back up into the well farther as you drop the front). It should able to clear the roller support when you pull the centerboard forward. Be careful, it is heavy. I put a safey stap (tie down) under it to catch it at various points. It may even drop quite a bit at the rear when you remove the roller even though it might be cleated.
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