That's a lovely boat Agent9. Congratulations.
If it's not a budget killer, it is a good idea to remove the mast. With the mast down you can take off all the rigging and bring it to a rigger to make the new rigging. Also, it will give you a chance to thoroughly check everything attached to the mast, remove and re-attach whatever shows signs of corrosion, inspect and replace the sheaves at the mast head and, if you don't already have one, install a PVC pipe conduit inside the mast for the new wiring. Check the lights and VHF antenna as well. All this is easy with the mast on the ground.
SF boat works is $200 an hour for the crane billed in half hour increments, I assume I can do the prep and get it off in an hour, but not sure. I think I am going to consult with a few riggers and see what their recommendation / preferred process is.
The lifelines you can replace with pieces of the old rigging. They will be much stronger than the original plastic coated lines.
Great idea! I love this.
I would think installing a new bilge pump and automatic switch should be a priority (not expensive). Then inspecting and repacking the stuffing box. Change all the hose clamps on the stuffing box regardless of their appearance. You can replace the stuffing in the water, but it is more difficult, Pre-cut the packing flax so you can work quickly when you pull out the old packing. I recommend the gortex packing that is pretty much dripless.
The bilge might be a project this weekend, I really want to hold off on a haul out to do the whole stuffing box, and I feel like that is the safest approach. The bolts themselves look a bit nasty (might just be grease and salt water all over them) and I dont know what I would do if the bolt snapped / stripped / etc when I was monkeying with them.
Next I would inspect every through-hull, hose, hose clamp (just replace with new) and the steering cables, sheaves and anything else hidden away. At this point you can be confident that your boat is safe.
I have inspected everything from the interior, I see evidence of tiny dribbles on a couple of the through hulls, nothing that wouldn't evaporate before hitting the bilge. When I do hall the boat out (hoping to get an idea of how the bottom paint is looking when I have the hull cleaned at the end of this week so I can assess) I will do a thorough inspection of everything.
Then go sailing and see what else needs attention.
Post some pics when you can!
I REALLY want to be out sailing instead of doing mental calculations of what its going to cost me to get the boat there
Thanks again for all the feedback.