There is really nothing wrong with starting with a trailer boat.
Think how many people stretched themselves on real estate and became miserable. I started with trailer boats (beach cat then a Stiletto, which isn't really trailerable) and I wouldn't have missed the expereince for ANYTHING. They are cheaper to operate, can "go to the weather at 60 mph" to see new places, and will teach you to sail. Some are quite seaworthy and many can take you far.
Then move to something more comfortable, with all of the knowledge gained.
Sail Delmarva: The Merits of Learning to Sail on a Small Boat
Sail Delmarva: Stiletto Stuff
If you still want the in-water boat, look for small work boat marinas and unfashionable places. Often folks have a few slips behind the house that they rent out. You'll have to do some looking, but the savings can be huge. I stay in such a marina and it is ~ 1/3 the going price.
Sail Delmarva: Catamaran Row
(when asked how he reached the starting holds on a difficult rock climbing problem that clearly favored taller climbers - he was perhaps 5'5")
"Well, I just climb up to them."
by Joe Brown, English rock climber
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