Jake, that doesn't look like it would work. The winch end seems so short compared to the mast end, and the mast end being so close to the base seems like it would be a huge amount of weight to push up. I think 2" tubing would bend pretty soon. Plus it you go past the point shown on your diagram the mast would start dropping again. I know my Hobie 18 mast would not go up this way. It seems like you would need more leverage on the pulling end and more thickness on the pushing end.