Re: new to me 1969 Cheoy Lee Offshore 27
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.
The lifelines you can replace with pieces of the old rigging. They will be much stronger than the original plastic coated lines.
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.
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. Then go sailing and see what else needs attention.
Post some pics when you can!