First, do NOT get out of the bosun chair! Ever.
Second, you should always go aloft with a safety line. In this case, that would mean the jib halyard. Drop the jib and attach it to the bosun chair along with the spin halyard. Take up slack on the safety line every 4' or so as you are hoisted.
Try to avoid using a shackle to attach the halyard to the chair. But in this case, you may have no other option if the jib halyard is also wire-rope. The preference is to tie in using a bowline. This may be a great opportunity to replace the halyards with all rope if they're older than about 10 years or if there are any kinks or meathooks on the wire.
It's not preferable, but you can put wire around a winch, but you'll need to double or triple the number of wraps. The winch finish may become scared as a result. The PO on both my boats did this and there is only slight scaring of the finish.
To feed the halyard, you'll need to run a tracer line if you have internal halyards. Take 1/8" nylon twine and tie a fishing weight to it. Feed over the sheave at the masthead and let the weight drop to the exit hole near the mast base. Use a bent coat hanger to retrieve.
If you have external halyards, just fish the halyard over the sheave. And pull out the forward side of the mast.
Be safe, go slow and always cleat both halyards as you go aloft. That is, every 4' or so, have your helper cleat the halyards. Old wire-rope halyards like Catalina used make me really nervous and I'd prefer to use all rope and a bowline. Time to upgrade.
Sabre 38 "Victoria"
Last edited by Sabreman; 07-23-2013 at 05:25 PM.