There are some 'beginner's naiveties' that crop up as repeatedly as this sort of thread occurs. The thread starters seem sincere and many, like you, have some sailing background.
The missing element in the quest for a decent (older) used sailboat is pedigree
. And, you'll get a mixed message about that from the on-line community just like you would get chatting with other sailors on the docks, too. There are owners who can articulate why they chose their make and model and actually know it's weakness and (hopefully) its strengths. I have found that less than half of owners have this level of background and knowledge. And some of those are loud and adamant that their boats are qualified to sail in coastal or offshore waters. (sigh)
The part that trips up the beginning buyers is the basic fallacy that "all sailboats are the same" in engineering, construction, and sailing ability. i.e. if they resemble a "sailboat" at a distance, they must the same, or any differences are not significant. (sigh, again)
Given that the vast numerical universe of used boats is left over from the heyday of building, during the fuel crunch of the 70's, and that the numerical majority of those boats were cheaply built, resurrecting one nowadays can be both chancy and expensive.
While there were whole brands with the requisite design, engineering, and construction techniques that are as desirable today as when they were built, they are not the majority of craft on the market.
Lots of buyers seem unconcerned about poorly-engineered hull to deck joints, for instance. Yet this will have an outsize influence on maintenance as these boats age beyond 40 and 50 years. Same thing for actual design. While it's generally better to buy a boat designed by a NA, there were a host of smaller boats drawn up by unqualified builders or even marketing people. Do your research, too, when it comes to the designer. I know of one 'name' designer that designed some exceedingly mediocre small sailboats for a now-long-vanished company.
I have several friends who have paid 50K to 100K in full reconstructions of boats from that era and now have craft that would take around 300K to replace new. If considering a boat in the under-30-foot area, the initial cost gets lower, but the cost per hour to fix things stays the same. A sailor I know that has put a lot of his time and money into maintaining and upgrading a classic 35 footer sez that there are three requirements to do what he (and most of us here) have done. Skill, Money, and Time. You must... have two out of the three. Now granted, there are owners with only money, lots of it, but their numbers are statistically few.... and scarce on the DIY sites like this one.
And.... after all those considerations, you still have to deal with worn-out (major!) construction stuff. Unless you plan to become proficient at glass work, you will be paying yard rates @$100./hr to have chainplates replaced, mast bases rebuilt, and spongy decks recored. No matter how good or ill the original build, ignorant prior owners may well have ignored the need to rebed ALL of their deck fittings and ports... leaving you with hidden moisture and rot. This particular sin does not have to happen, but it does, and to some otherwise fine vessels.
As the aged knight in the movie told Indy, "Choose wisely"
Finally, be prepared to find exact models of a given boat, priced at 4K, 8K, and 12K. And that each one is worth the money.
Often it's far better to spend extra for a well-maintained one and actually get to go sailing rather than spend the next two years working on one (and then finally burn out and dump it).
Happy Hunting. It took us a full year to find our current boat, and we saw horrible things for sale, many at respectable brokerages. The traveling was fun but some of the boats managed to be both weird and depressing, simultaneously.
Some were overpriced and some were underpriced... the later for all-too-apparent reasons.
The "search" worked out well for us. We found a (neglected fixer upper) very high quality boat from a high end builder. Lots of clean up, and for the first several years a number of new parts... and we still have it over 20 years later. I have done most but not all of the work; some things are best done in the yard.
I guess that it's kinda like houses -- look for strong foundations and footings...... it's vastly cheaper to change the color !
ps: and since this is advice over the 'net, YMMV !!
pps: and if Jeff_H seems to say something different, he's probably right... or at least as 'right' as me.