Consider a smaller trailerable
Ask yourself:Will I mostly daysail or do alot of overnighters/weekend/extended cruising?Will I keep mostly to harbors, Lakes or other protected/semi-protected waters or will I want to go off-shore (even coastal)?How many people wil I typically sail with? A family of 5 or just me and a friend?How big of a tow vehicle am I willing to own? Find out what the towing weight of any boat you are thinking about (boat, trailer, motor, supplies). Some can be towed behind a normal sized car, others will require a maxi-pickup or SUV that will cost alot and drink alot of gas.There is a sort of "Peter Principle" in boating: Some people will buy ever larger and more complex boats looking for a bit more storage, capacity, ability to sail offshore or just because they think they should and then find that they sail less often, spend more time on maintenence, cannot singlehand the boat, spend more mony on upkeep etc. Generally enjoy the sport less rather than more. That's not always the case, some people move up from day sailors through large trailerables and on to ocean going craft and love every minute of it.Rule of thumb: Cost of ownership will increase linearly with displacement, not length.I sail a midget sized cabin boat (Compac 16) and would love to have more cabin space, greater ability to go coastal and handle seas. But I want to retain the 30 minute set up, take down, the ability to tow behind a normal car, the small space it takes up in the driveway, the short time it takes to wash, the really cheap outboard needed to push it, the smaller, chaeper sails etc. This boat is really too small for most people unless they mainly want to day sail in protected water, but remember that everything about boating is a compromise.