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Best 2 days of boat ownership are the day you buy it and the day you sell it.
Expect to spend 20% on repair cost each year (depending how much you sail, of course. I am quoting every weekend sailors). Docking is like any other property - location, location, location. Impossible to quote.
Unless you are already very knowledgeable about sailing and know exactly what boat you want - join a sailing club. Best way to learn, hone your skills and meet fellow sailors.
By smaller boat, do you mean a sunfish or a hobie cat? Or are you talking cabin sailboat?
I was in a sailing club for a season, really fun, only about $150 to go out every weekend.
I was quoting a 14 foot plus sailboat. Learned on a sunfish at 15. Lots of fun, but be prepared to get wet.
A1, same. I have 2 sunfish and a hobie. Would recommend learning on a smaller boat. As A2 points out, you can learn how to sail relatively inexpensively without having to buy a boat. Once you decide you like it, the concept is the same regardless of the size of the boat. I've never owned a larger boat that I have had to dock, so I'll defer to A1 and others for cost.
Easy to find a sailing club in any major east coast city and it will likely cost you <$1000 per year
I have a small boat at a yacht club (<25ft). Older boat, not meticulously cared for. Spending 2500 a year or so fully loaded. A good sailing club will run you comparably. Also, my boy is for sale presently (movin on up!), so I can tell you it is a worthwhile expense :)
Sunfish is good starting out, but you'll get bored quick. Look a the Laser or Laser Radial, both fun, fast and challenging in heavier conditions. About 6k for the boat and upkeep shouldn't be over $100/yr.