Well, we are living what one of the things you are considering. Your boat is essentially just like ours, a 1973 Venture that turned out to be a wreck with blown out sails and a cracked up rudder. The coat of house paint must have dazzled my uneducated eye. Got it for 1100 with a decent running old engine. Should have done my homework first. But we sailed it and enjoyed it very much. Plus its roomy, very light, easy to trailer around, gets into seriously shallow water for its size, and easy to rig up and down the ramp. Also the keel was in good shape.
Money and time were the issue - and remain so. So the Admiral and I had to make some choices. We are hooked on sailing and are married to a wreck and a low supply of available boat bucks. We planned on having a boat of this size for at least 12 years. What to do???
I took it as a challenge - make my own boat from this shell and do it in a affordable manner.
For trailering around this model boat works really well and the large pop top really adds. Plenty of room inside to tailor to exactly what we want - RV style. The keel is iron (yea!). And its fun to sail. Mediocre trailer that needs eventually overhaul. We didn't feel like the hassle of sell shop finance buy adventure so we went with the restore as we sail strategy on the cheap. Developed the must should nice to do list and got on it.
The method is every spring as soon as the thaw happens its into the boat for cutting grinding sanding gluing grinding sanding gluing gluing gluing grinding sanding sanding sanding sanding painting. Whatever was priority, planned or discovered, got done no matter what by late may for splashing. The rest of summer and fall we sail with little repair work being done unless compelled.
After four years the worst is over. The boat is finally structurally sound and reasonably dripless.She still isn't real pretty but those items are soon moving from nice to should in priority.
The grinding inside is awful. I ground almost everything inside this boat to get the finish I desired. At times I dreaded going out to the grinder again but I endeavored to persevere. I didn't waste money on the west system koolaid and used the stuff the boat is made of. I'm approximately 6 gallons in. I'm ok with just good quality plywood for cores - its better than what Mac used.
Now that the interior has been ground and faired - its really nice and our floating RV is beginning to come together. At the cost of some $$$ as available, lots of elbow grease, every available early spring hour that is environmentally conducive to boat restoration, and a keen determination to make something better than it was for no return other than personal satisfaction and the love of sailing a heavily modified custom built easy to handle trailer sailor.
Cushions, rigging, and sails I expected to have to replace - 50 year old boat and all. The boat sails and the cushions cushion - not an emergency. Also, those are the things you change as you make a boat your own I think. Most of these items are on the nice to do side of the list and are finally being splurged on here and there. We celebrate those things.
This year cushions moved from nice to should and we spent $600 and got them all (veberth/cabin settees). Unfortunately vberth rebuild and mast step recore became urgent. But its done and we can splash anytime now and its going to be great.
Its slowly all coming together and it makes me smile and dream about before I go to sleep. The wind the waves our little sail boat...ours mine mine MINE MINE!!!
Theres more in the value of a sail boat than mere money. Its a mans statement to God.
As I look back now: I would have taken ONE season off and just restored the structure. Take the deck off and take her down to the stringers. The deck isn't THAT hard to get off safely (people have done exactly that with ventures), just takes will.
The grinding and reconfiguring of bulkheads and lockers vberth, and core repair would have been much easier and likely faster and less aggravating.
But I sure know my boat. And the prettier I make her the more I smile.
ymmv