Before you jump into anything....
Whats the biggest boat YOU have sailed on your own and how much experience do you and your crew have? Why do I ask?, because ive seen people jump into boats that size because of what they want in a boat (because of some "dream" they had) instead of what they can actually handle. These boats end up never leaving the dock if there is so much as a cloud in the sky and become bird nests.
25' is the largest sailboat I've personally sailed. I fully understand that this is a sight shorter than what I'm shopping for, but I feel that in order to get experience, I need to actually get on something larger. Sticking my thumb out in the breeze hoping to hitch a ride on someone else's boat has me spending too much time on the shore. Are some of the boats I'm shopping for too much for me to dive into trying to single-hand right out of the box? Yes. That doesn't mean I lack the ability to learn, or the confidence that I'll eventually get comfortable with it. Prior to that 25 footer, I had 0 experience at the helm of any sailboat. I realize that I have a whole lot to learn, but that didn't stop me from getting out there and to single-handedly squeeze all I could out of that thing, and walk away wanting more. I'll approach a much larger boat in a different way of course, but a dock queen she will not be.
Also, I would familiarize yourself with what things cost on a 39 foot boat ie; sails,furling,engine overhaul,glass work,rigging etc...minor and major (things happen) Call around to get an idea because any boat from the 70's will eventually need it.
This is actually one of my main concerns, and why I'll be holding over a fund specifically for such issues. If I move aboard, then that would free up a good amount for the fund. Previous hobbies (racing cars, motorcycles, flying airplanes, etc) all had ungodly high costs for little return to justify the expense. Sailing strikes me as a bit different as the return thus far has been tremendous. Plus, air is still free, so at least I save some there. I've checked some pricing for various items for boats of this size, and do see that it can get out of hand really quickly, but believe that if I can just get it to a point, then I should be able to better grasp regular maintenance items.
My boat is a 76 and did very well on its survey when I bought it two years ago.I have put enough money in her in the last two years to buy another one and I still have more to go before its the way I want it.Worth every penny because of what I paid for the boat and sentimental reasoning but worth mentioning.
The c&c 39 was a well built safe boat thats quick and points well but who knows what may have happened in the last 30+ years.Get a good surveyor.
I wish you the best of luck on your search.
Thanks for the advice, and I do plan on getting a good surveyor to check out whatever I end up buying. I'm taking this process seriously and want to avoid too many surprises, so I appreciate hearing from all of you guys.