Thanks for the feedback everyone. Looks like I will be dropping my mast! As a commuter, the problem is when I have to do work to figure out what parts I need, order parts, then install them after they arrive. With a 4-hour drive in between cycles, some repairs can take months (replacing the port lights was a bear...)
I should clarify that the "offshore racing" I plan to do, while competitive, is more of an "offshore challenge" - mainly overnight runs in the 90-130nm range (some of the classes have time deductions for size of fish caught, if that give you an idea...). We race on smaller boats in Atlanta, and mainly day-sail the J/30, so it doesn't get quite the same level of attention.
Also, all of the yards around Charleston will not let you TOUCH your boat while it is at their facilities. The closest self-service yard is a couple inlets south.
It sounds like if I have the spreader kit and tools, light bulbs, tape, and the new halyards ready to go, and if I can find a local source with a variety of sheaves, I should be able to knock it all out in a single day.
Thanks for the help!
-Dan