If $350 presents a problem for you at any time, you can't afford a sailboat of any kind.
There's a very good reason why $1000 is called a "Boat buck".
Here's a fresh, concrete example. On Tuesday two friends & I brought my 30' boat down from its berth to be hauled for the winter.
Out of pocket expenditures for me were as follows;
$20 - Food & drink for the trip.
$15 - Gas for the car for the trip.
$10 - Diesel for the boat.
$350 - Haul, pressure wash & block the boat.
And that's only the start - now the real expenses begin.