A friend just did it
A friend just did this on his Cal 29. It was a lot more time consuming than he thought it would have been, but it looks great. He removed all of his old standing rigging and had a rigging shop make up a new set, using the old as a pattern. I don't know how much extra this cost, but, for me it would be worth the piece of mind. Plus, they pay for any mistakes. My experience is that, no matter how careful I am, I always end up doing part of a job at least twice before it's right. Unless money is extremely tight I wouldn't make my own rigging. Make sure you use open, bronze turnbuckles instead of the original, stainless steel barrel type which are prone to hidden corrosion and galling (seizing). In terms of painting, if your mast currently isn't painted, I'd reconsider the idea to paint. It is very time consuming to do right but if you do, preparation is the key. To me, it's kind of like the roof on my house. I look at it a lot right after replacing it but after a while it fades into the background. I'd save my time and money for something more functional. My C-30 is aluminum and I think I'll keep it that way. While you're at it, consider replacing your VHF antenna and other masthead gear with new. One more thing, triple check everything. On my friend's boat, we had the mast up on the crane and as we lowered it to the mast step, he noticed that he had replaced the VHF connectors with two male plugs, so off to West Marine, again, this time with the mast dangling from the crane.