Notice:
The advice given on this site is based upon individual or quoted experience, yours may differ.
The Officers, Staff and members of this site only provide information based upon the concept that anyone utilizing this information does so at their own risk and holds harmless all contributors to this site.
Unless you have a 'robust' spinnaker halyard, the bosuns chair will need to be suspended from the main or jib halyard, which runs over the sheaves you're trying to replace.
IMHO: It's really not that hard to lower the mast on a 25' boat and it will overall speed the job up a lot. It is pretty easy to lose stuff in the drink at deck level, let alone at the masthead.
its easy to do but I think the mast should come down. I backed my boat into the slip, lowered the mast, leaving the mast base in the tabernacle. With the mast crutch on the dock, I quickly changed the sheaves.
Beware, there is a divider plate between the sheaves plus stainless washers. I pulled the pins and some of these bounced off the deck and into the water.
I went with CD 3/16 nylon sheaves and also recently bought a new divider plate (I've been using the boat a year without one).
Notice: The advice given on this site is based upon individual or quoted experience, yours may differ. The Officers, Staff and members of this site only provide information based upon the concept that anyone utilizing this information does so at their own risk and holds harmless all contributors to this site.