Agent9, when I pulled my deck-stepped mast it was about 15 minutes of crane work. You can remove a lot of stuff yourself before the crane arrives (boom, sails). When the crane arrives and holds the mast you just release the standing rigging at deck level and away it goes! Is your mast stepped on the deck or keel?
Deck stepped, I assume this makes it a bit easier to remove.
I agree that doing the stuffing box on the hard is the best option. You can tackle that along with replacing through hulls and valves as well. If you're quick about it you can do most in a day, then another 2 for painting the bottom and you're back in the water. As much as I understand your desire to get out sailing, seeing to these problems first will only take a few days and you'll enjoy the peace of mind when you are out sailing, knowing the essentials are taken care of. The rest you can deal with in the water, little by little, without interrupting your sailing. As you're in SF, you have a nice long sailing season so you won't miss much of it doing the repairs now. Just my 2 cents.
Rigging is immediate, I really want to get a divers opinion on the bottom of the boat before committing to pulling it out of the water. If she needs paint / blisters patched as well, I am going to have to plan a bit more for time / work space. I may do the top paint at the same time and make a jolly old painting week out of it. Otherwise I am just going to have it pulled and to deal with the stuffing box, and deal with the through hulls. I would love to deal with all the bottom painting once it gets cold and nasty at the end of the season.
A quick side story. A friend of mine bought a Dufour 35 that was rather neglected. He couldn't stand the sight of the boat in such a state and went ahead and painted the boat, got a new mainsail, new sail covers and other cosmetics. He blew his budget before he really had a chance to see all the problems. As it turned out, the main problem was the many leaks, which he should have dealt with first, before anything else. The boat is now literally waterlogged and rotten (decks, bulkheads, cushions etc.). The moral of the story is: do what is essential for safety or maintaining the integrity of the boat first (to "contain" further decay), and then set about doing the rest at your leisure and as money allows.
Great little story,and i am sure it is fairly common. I am not looking the prettiest boat out there, I am looking for a fun boat with some character that is safe and I trust. I have a 72 BMW R60/5 motorcycle that I have rebuilt which is the same kind of story. I know the bike inside and out and I like her dents and dings and general patina. I trust her mechanically because I have done it all to her. Given, I do not have to depend on her floating, and she has not been sitting in salt water for the last 40 years.
On a positive note, a boat like yours will be easy to maintain and will cost quite a bit less to bring up to bristol condition than a larger boat. It will also be one heck of a nice boat! Post those pics!
That is what I am hoping.
On a really positive note, I took my jib in to be patched, and the wonderful woman (Harriet) very gently told me that it was more or less beyond repair, but had a set of sails in the back that will my boat which she gave me an AMAZING deal on. Already a HUGE fan of Harriets Sail Repaint in North Beach San Francisco. So at very least I have a new set of sails I am confident in....once I get to the point of using them.