Regarding
pricing: All boats over a certain age, maybe about 25 years in round numbers, see quite a drop in market pricing. There are both practical and illogical reasons. Pragmatic point: there are very few used boats maintained in "original condition" -- small %. I have managed our 150 moorage for many years, and can count on two hands, max, the boats that are 100% turn-key. Degradation is so slow for most major maintenance items that owners turn a blind eye to it. Worse,
entropy for anything in or on salt water moves faster than for something stored on land. The decline is slower for boats used in fresh water, but still going on. There are enough knowledgeable buyers to keep the price low for this 96% of the used market. In a declining market, as we have had for over 20 years in sailboats, there are also fewer knowledgeable buyers. Due to a mix or societal and economic factors, sailing as a family sport has trended downward for many years.
And then there is a factor that very few brokers will even mention, unless really prompted: basic
Engineering, Build Quality, and Design for Sailing.
Once the market started to skew towards large-interior and mediocre-sailing designs that were selling to people with limited sailing knowledge who simply wanted to view themselves as "sailors", builders found that they could build weaker and slower boats and make a better profit in this constricting market. While every modern/surviving builder has a few models actually known for their sailing ability, most of the "Hunta-Cata-Benolina" boats are aimed at this sailor-wanna-be market.
Note that larger boats now are marketed specifically to a second home market. The owners seldom leave the dock, and those that do use their boat in a somewhat narrow Performance Envelope with a wind range of 10 to 15 kts and seas under 2 feet.
Good news is that their second home sails reasonable well in that specific envelope, absent the ability to point very well.
Like it or not, this has affected the market like a sort of "Gresham's Law". Knowledgeable owners of Good Old Boats keep them a long time - several decades is not uncommon. And in many cases, they invest serious $$ into upkeep.
New sailors, including those who really want to sail, see few good boats at dealers and brokerages, and the brokers (needing a sale in order to make a living) are not going to spend/waste too much time educating a buyer on the boats. After all, if he/she has an inventory of 20 cheap boats and one Ericson/Sabre/Hinterhoeller/C&C, (and some others).... the sales time has to go towards making a living.
I used to know several brokers who were in it full time when I did some part time brokering of small boats, and the wry humor was that for a typical unrealistic shopper, the Third Broker would sell him a boat, after he initially rejected the well-intentioned advice from the first two, and was embarrassed to return to them to buy something!

Which is a roundabout way of saying that there have never been a very high % of knowledgeable shoppers. And was back in 1981.
Now, decades into the flooding of the used sailboat market with poor boats that are accepted as 'normal' by brokers and magazines needing to keep their slim ad revenues working, The good boats have been devalued because, in effect, they are less suited to a live aboard lifestyle.
This can be good news if shopping for a high-end boat with actual sailing prowess.
Stability -- for better or worse the public conception of this has never been too informed, and it's worse nowadays. If you have a hull with slack bilges it will heel some when you step on the deck. This is initial stability. When it heels to 15 degrees going to weather and then is really reluctant to heel any further that's final stability. Newbies really like something that does not move when they step onto it. Once they sail a lot, they will begin to see the tradeoff. Starting out in a Ranger 20, I raced and cruised for five years amidst an equally large fleet of Catalina 22's. The Ranger would heel and they stiffen up and steered easy. The Catalina has a flatter bottom and a harder chine and felt more 'reassuring' when you stepped aboard, but had more helm difficulties as the wind went over 12 kts. It also had, due to this shape, more wetted surface and was slower in light air.
Owners of either design were very happy, but for somewhat different reasons.
Aside: a older smaller Cal-20 fleet would race weeknights with us sometimes. Faster design on some points, but the Rangers could catch them off the wind with spinnakers up. Lesson was that ALL boats are compromises.
Condition is always going to be very important, but for design alone, keep in mind that in many "lists" of the best production sail boats of all time, the King-designed Ericson 35-2, is always there. It was ahead of its time in some key ways, and avoided the disadvantages of many of the other IOR-focused boats of the era. Yes, that is just an opinion; worth about one cent with Monday discount.
Whatever you buy, do stick around and talk to us! You are asking the 'right' questions.
And... Stanchions.... Back in the early 70's (date not remembered) racing rules started to require lifelines. This raised the selling price for all boats. With a minimum distance rule-specified between stanchions, many builders would seize the wire to an outer shroud at that point, since shrouds on the boats designed in the 60's era had chainplates at or near the toe rail. As the IOR "look" because popular with buyers, the wider boats needed another stanchion at that point.