Hey Dan this is yet another problem that I overcame last year cause I to like to hoist the ol mast up by hand and solo. having the girl freind around every now and then just wasent happening for me so I decided I needed to be able to do it by myself LOL. Any way I just bought the new stepping link that hobie makes it has a hoel for the 14 and 16. One question though how old is the mast base on your mast because kinda like me you have an old boat dosent mean its bad though right
I know on the really early boats such as mine that the mast base had a hook design rather than a hole that a pin went through and these were modified by drilling a hole in them later because the hook would inebiably break. WEll I just replaced the whole mast foot on teh end of the mast with a brand new one. With the new foot and stepper link mine goes up just fine solo I just lift her up and stop just shy of completely vertical cause much past this point the pin will bind in the link because you are then pulling the link forward with the mast. So just bend down holding hte mast with your left hand and pull the pin when its almost to the vertical position. Thats what I do then I shove it all the way to the vertical so it just stays there grab the forestay jump off the front of the boat and pin it in to the bridals.
That has been my meathod any way but I think that earlier post about mabye tin ga line to the trailer and holding it tha tway till you get it pinned is a really good idea as well. But I dont think its worth investing in a ez stepping system I mean hell that mast is pretty light Devon can move it around thats my girl friend so most of those ppl with winchs and what have you are just lazy. Hope that helps.