I've read all these posts, and most don't answer the question. It's not "is it better to buy a new boat than a used boat." It's not "is it better to buy a boat that needs some TLC than one that doesn't." It's not "Are older boats better boats than new ones." It is simply "Is a major fixer upper a good choice over a similar boat that has been maintained or already fixed up"
If you LIKE spending time and money on an old boat, then yes. It's not about the money, it's about what you want to do. If you want to sail, then NO, because you aren't doing what you want. If you want a 1980's boat because you like they way they are, or because you can't afford a 2012 model, there is no question -- a well fitted out 1980's boat is a much better deal than a poorly fitted, poorly maintained boat in need of refitting.
I looked at a 1980 or so Ericson 35. They were asking 20K for it. I offered 5K, and I'm glad they didn't take the offer. It would have needed an autopilot, roller furling, new sails all around, new running rigging all around, new dodger and bimini, new rub rail (it was half on the ground), and who knows what all. For the $20-30K it would need, I could have just bought a boat for that amount that would have had all that and self tailing winches and refrigeration and no rust stains on the countertops and so on. And I would have sailed it the first year. Yes, a better boat wouldn't have had NEW roller furling or all those thing -- but the used ones would still last a decade.
The boat I bought was a Sabre 34, well equipped, so at least I'm not spending money on "stuff." I paid half what they were asking, and 1/3 of what a comparable boat in good condition would have cost. But I've got over $5K in storage fees while I work on her. Work I can do, and do well. Work that will make me happy with the product. Work that keeps me from sailing the boat. Work that has become an "obligation," not a "hobby." At this point, with many hundreds of hours of labor, thousands of dollars in material costs, and thousands more in storage, I have a boat that is worth less than I paid for her (she's now a work in progress, which has zero curb appeal). And when I'm all done, I'll have paid (purchase, materials, and storage -- forget labor) what a good condition Sabre 34 would have cost, and I'll have missed a few years of sailing in the process. And frankly, I'm not sure she'll be much (if any) better than the good condition boat would have been. She'll still have 30 year old gel coat, furling, winches, and engine, she'll still have old sails, she'll still have crazed ports -- she'll still be a 30 year old boat! Just with the major problems fixed. And that other boat would probably have come with an anchor windlass, perhaps snazzy LED lights, maybe an asymmetric 'chute, or a few other toys my neglected boat never got and aren't (to me) worth the price to add them as new improvements -- but would have been great if they came with the boat at little if any additional cost.
No, my choice was penny wise and pound foolish.
Harry