Some people take care of boats while others do not. You can have two of the same model and year boats sitting side by side and the difference can be night and day. One can be meticulously maintained - the other in deplorable condition and, of course, anywhere in between. One boat can be extremely well equipped while the other has basic gear (and the age of the gear will have an influence). One boat can be fresh water while the other is salt water (salt water is tough on boats). Boats that are sailed in Wisconsin or Minnesota or the Dakotas, for example, are in fresh water, are sailed only 4 to 6 months a year (give or take) - and hence are stored for the balance of the year - not in use and not abused, while a boat in a warm climate is used much more, stored much less and is exposed to wear and tear a great deal more. Some boats are more popular in some areas than in others. If there is a demand for a certain boat, sometimes that will influence prices. When looking at a boat listing, one has to be very subjective and must look at the boat and make comparisons. I happen to own a very nice used boat that has a varnished interior, is clean as a whistle, is equipped with upgraded winches, lots of electronics and cool stuff, for example and I would demand much more money than some other boats of the same make and year that have hardly any equipment, are not kept as well, have rotting components like bulkheads, on and on. You pay for what you get, I think. If you want an exceptionally nice boat, you will have to fork out more money to get it. The alternative is to buy something less and then spend more money making it look like the boat you really want. And then some buyers aren't discriminating. They just want something that floats. And, of course one's budget enters into it. But, then, you buy what you can afford. I am not trying to be arrogant about this. If you buy what you can afford and it isn't what you really want, well, good for you. Enjoy it, make it better and then one day you can get more of what you want. And, someone starting out perhaps hasn't formed any decent priorities about a sailing vessel. Priorities change as a person grows with the sport and as that process continues, so does your taste in what you want in a boat.