I will give you another view on costs associated with an older boat. Comodave, a very expreienced and knowledgable boat owner, well respected on TF gave you some rough extimates that in my and my friend's experience are on the low side. Not to argue with Comodave, just a second opinion.
So much of the costs of hiring work done are based upon where you have the work done. You are in California, I think that is a very expensive place. I and my friend are in the Puget Sound area, another very expensive place.
Regarding leaking decks. My friend has a KK42. The upper deck suffered from leaks mostly due to bad bedding of stanchions, fly bridge etc. No teak decks up there, but the idea of lots of screws leaking is a similar problem. Cost to tear the upper layer of fiberlass off, replace the rotted core and new layer of fiberglass to a high standard of work. $70K last winter in Anacortes Wa. I don't think he got screwed. I visited the yard early in the project. There were 3 skilled techs digging into the work. $155 / hr X 3 techs X 8 hrs a day adds up to many thousands of $$$ in a big hurry. One day at those rates is $3,720. His main decks are teak, lots of screws. What will happen if those leak? I shudder to think.
Regarding costs of owning, maintaining and upgrading an older boat. I have an 83 Californian, not the same as your target purchase, a bit older. I've had the boat since 2019. It's been a mix of DIY and professional work to bring her up to long term cruising fit. She's not done yet. Total cost of professional work has been to date over $140K. Total cost of DIY can't be measured in $$$. It seems endless. I'm worn out and tired of always making working on the boat the #1 priority on how I spend my time. I used to enjoy it.
This was a boat that appeared to be in very good shape, surveyed very well.
Will you have the scale of problems I and my buddy faced? Maybe. Maybe not. But go into the purchase of an old boat with your eyes wide open. Understand what your upper limits are. Have an exit plan if big surprises are found. Understand that very little of the $$$ you pour into her will be returned to you upon sale. Maybe with the case of a GB the purchase price because they are popular sought after boats.
I've heard the 10% maintenance rule many times. I'm not sure how accurate it is, especially on older boats.