For me the key to a second hand cheaper (
So you might see an Elliott 7.9 (as mentioned above) for $20k but you get what you pay for. I know when I purchased my E7.9 as a project and then spent 2 years completely rebuilding her at significant time and $$, there is no way I would want to go back to owning a shitter. Thats why you might see an Elliott 7.9 for $20k and one for $50k+. By the time youve spent $15k on a new motor, $10k on paint, $10k on sails, $5k on electrics ++++ it adds up.
So my tip is to buy the boat in the best condition that you can afford.