+1
This is the route I'm going. I have replaced the drive shaft, cutlass bearing, installed PSS, self steering wind vane, AIS, all hoses below the water line, every through hull have been serviced and or replaced, rudder post repacked, steering (cables, armature, pullies) disassembled serviced and reassembled and tuned, pulled all standing rigging, resized and replaced because the mast was not properly seated on the mast step and settled 2" after a vigorous sail (30knts close hauled for 6 hrs)...this was something I and the surveyor missed when I bought the boat. Stupidity?...maybe but shit happens. Things will not reveal themselves on a boat until you push her. And I just barely got started. I've pulled the boat twice in one year. All the work I have done myself and some of it has been a steep learning curve, but I'm glad Ive done it. I know my boat. I have confidence that what I fixed was done properly and safe. If anything I probably overthink shit too much. I guess I'll figure that out too.
Buy a boat that speaks to you and that has a good reputation, sail the shit out of it and break stuff. Figure out what works and doesn't work for you. Strip off stuff you don't use or need. Add what is required and what works for how you sail. Sometimes you'll sail the boat and other times the boat will sail you. Make it yours. Start now!