Originally Posted by Faster
Another vote for simply switching to rope that will pass over the sheaves you've got (unless you've got reason to believe there's a problem with them otherwise). You could make them long enough to run back eventually, though that will leave a bigger coil at the mast in the meantime.
If your reef lines are at the mast/gooseneck area then there's not a lot of point in running the halyard back, esp if you sail alone much of the time.. So to make leading aft effective you'll be best to lead the reefs and the halyard aft at the same time. If you do have at least one helpful crew then you can work around having the halyard in the cockpit and the reef lines at the mast, esp if you have some sort of self steering to help as well.
The fact that the wire makes it to the winch itself is more about being bad news for the winch drum than anything else.. you can cut the wire short, recrimp the eye and shackle as long as the rope tail is still long enough to reach.. but I'd get rid of the rope/wire combos in any case.. no need nowadays, and you'll avoid bleeding from jaggers now and then.
With all rope halyards, you can forego any sort of shackle and tie the halyard on, with extra length you can shorten it many times in the event of chafe - and no heavy shackle to smack you upside the head if it gets away on you..
My reason for potentially replacing the sheaves is this: Several weeks ago I was crewing in a race onboard a new Colgate 26. Someone got the main halyard tangled on a winch so I went forward to release tension on it. Based on the tension in my own sail hoists I grabbed the halyard expecting a struggle. To my surprise I was able to hoist the sail effortlessly, which leads me to believe that my own sheaves have probably seen better days. As for reefing lines, I have all the hardware in place but no lines. I've contemplated using 550 paracord to rig a reefing system up temporarily. I think I'm going to take advantage of how cheap Sta-Set is at the moment (eBay has it for less than .50 per foot), splurge, and replace all running rigging, leaving out the wire halyards. I have a number of spare snap shackles that came with the boat that I can use as well.