To buy or to rent, that is the question...
I feel your pain. I got my first boat some years ago after years of crewing on other people''s boats. Then a few years ago suddenly got boat fever. Went through nearly a boat a year. BOTH power and sail. Had two at a time. Whew. I am TRYING to cure myself AND trying to sell the boat I have now to go to a larger, classic, like a Morgan 382. Nice boat that can take me anywhere, classic lines, sturdy and much lower cost.
I think low upfront cost is a key factor. As you know, there are lots of expenses in owning a boat. You constantly want to upgrade and improve her and make her look nice. Thus, the logic is get an older boat in good condition that you can upgrade and make look good - something you would want to do anyway.
Just my $0.02