For the past 8 years I've been doing the same thing and have just a couple more items to finish up before taking it to the S. Pac. I'm a Jack-of-Trades but a Maintenance
Machinist as a profession. And I started working on boats, PBR's and Swifts, in Viet Nam (1969). Not to boast!
Here is my advice;
The rigging you can learn in time. There are courses you can take.
Avoid wood cored hulls, balsa or foam cored decks are OK. Choose the boat wisely, your biggest savings. Get one of a quality builder
, another plus!
If you can keep the boat in your yard or someplace real cheap
, it'll save you lot$.
You'll have to donate ALMOST all your free time to the boat work. If married it MAYBE a problem. It's all or nothing!
There are hundreds of abandon projects out there, let alone perfectly good boats that just need some TLC. hopefully you can fined one of those!
Keep an on going notebook with 'What to buy' and 'What to do' lists and carry it with you at all times. Pick up supplies while in an area. Special trips cost extra.
If your not sure what to do in a fix/refurbish, get several opinions. Your decision may constitute your sea worthy-ness/safety. The CF forum is a great research
Stay active in sailing. Crew or join a yacht club! you'll pick up ideas on what needs to be done on yours and keeps you up to date on technologies.
I put my boat in the water
, at least, once a year for a couple weeks. Doing so allowed me to proof my work (and to add to my lists
I don't know how much experience you have with boats but it maybe best to start on a small boat at first (trailerable) for a couple years and when you feel confident then move up to a bigger project
. You sound as though you have the good practical experience to do the work and it is a learning
process as you go. I've even seen some pretty shaby work out of the so called professional builders. After 40 years of working on boats one can say they have some experience.
I could go on forever but I'll let others pipe in. CF has a load of knowledge and you've run onto a good source info, besides I need to get down to the boat for more work.
BTW Welcome aboard!