Welcome aboard! I think you are looking for the right sized sailboats. The rest of the questions you are asking will have to be attended to by other forum subscribers. I'm certain you'll get some help from folks in your area because this is a great forum for good answers.
Kind Regards, --John--
it all depends on the age and price of the boat really. you can usually get 10 - 15 years financing with 20% down. anything over 30 feet will need to be kept in the water. you can easily get an online quote from boat US and their rates are competitive. if you keep a boat at a marina they usually charge between 10 and 14 a foot.