Agent9, you are approaching this in the right way. Too often, posters buying older boats are blind to the amount of deferred maintenance that needs to be addressed and the expenses involved with rigging, engines and sails.
As stated above, the best of all worlds is to have the rigger pull the stick. All the riggers I know will let you work on your stick while it is down and while they are making the new stays and shrouds. The downside is “mission creep” as you see that a lot of hardware is on the verge of needing replacing and how easy it would be to do some upgrades. I know, years ago I needed to replace a headstay and wound up stripping the sticks, painting them and replacing all sorts of hardware (and replacing the rest of the wire.) I recall that I overran that budget by 3X.
Without looking at your boat, I would say your cracked swages are headstay at the stem fitting and the bases of the cap shrouds and lowers. Your back stay has no crack. You have a low freeboard boat and the front is continuously getting doused in our Bay chop. Even with machined rolled swages, water got in and caused crevice corrosion. Sta-Lok and Norsman terminals by their construction will allow for more trapped water. Do you really want that maintenance item? Besides, your wire is pretty small (3/16, 7/32?) and easily machine swaged. I have taken the Biron Toss rigging class and re-wired one boat by myself. I won’t do that again. But if you are game I’d be happy to sell you a Loos Gauge.
I know that Biron too, has finally come around to synthetic life lines, but I remain skeptical. The fibers attract grime (I have a synthetic gate on my sugar scoop). You have a single lifeline, again small diameter, get wire (I prefer uncoated). You will be buying new turnbuckles and fittings anyway which is probably a majority of the expense. Standing rigging wire is a different construction than your lifelines and not flexible. If you use it in a lifeline application, you will not be able to use your gates.
Your packing gland should look something like this: All you need to do is tighten it less than a turn to stop the constant drip. This is an owner job and done in the water. If it is a full stop and still leaking, then haul the boat and replace. I am a little concerned that your through-hulls are leaking. If they are leaking at the hoses, replace the hoses and hose clamps (probably fifty year old clamps anyways). You will want to double clamp all hoses below the waterline. I would work on stopping all the leaks. In the meanwhile, leave your battery charger plugged into shore power. A cycling pump will kill a group 24 or 27 battery in no time.
As you can see from my signature, my boat is over in the east Bay and I am most familiar with those boat yards. Talk to your dock neighbors for recommendations about San Francisco Boat Works. Your boat is “classic plastic” and although you will never completely recover the money you spend in resale value, it will give you years of enjoyable service in the future.