I would recommend riding as many differnt boats as possible. If you plan on racing
or cruising spend time sailing with the Wed and weekend regattas as crew. Try to sail a variety of boats and if you find one you like try to get assigned to one several times to see and learn how she handles.
Boats feel different once the newness wears off and you start seeing what thing you like rather than what is already on the boat. Then buy the cheapest servicable boat. We found though we bought a nice boat at a good price
we were ready to change after a fe years once we learned what we really wanted and needed rather than what all of the sailing magazines and our friends convinced us we should have.
We swtich from a mono to a Cat. If we would have bought a new mono or a very expensive one we would have sold it at a loss or have been forced to keep it because we were to far into it financially to get rid of it and get what we really wanted.
Experince makes a difference.