Boats in general
Regarding a number of posts you have made, the reality of sailing is frequently very different from the fantasy of sailing. Before you jump in with both feet and buy a 35-40' boat, I think you would be better off with something in the 30' range first.
Even a 40' boat will not be 'luxurious' for 3-4 people. You will still have a fairly small and cramped V Berth forward, a small and cramped cabin aft and maybe a smaller and even more cramped cabin aft, or a decent sleeping space in the main cabin. The typical 40' will have 1 or 2 heads, a very small shower, a lack of hot water for showering, a cramped galley, poor closet space, and poor heating and air conditioning.
So, if you think a boat will make a nice summer cottage, think again. Then again, a boat allows you do go places, or go no where in particular, but have fun doing it. You can learn new skills, enjoy your self sufficiency, and spend time together.
I know lots of people who love sailing, and lots of people who don't like it. I also know many people who enjoy spending a few hours on a boat, but then want to go back to their comfortable homes.
So, before you get too involved, try to find you which camp you (and your family) fall into.
Regarding sailing locations:
The CT side of the sound is a great location. There is usually decent wind. August does tend to be light, but that's true for the entire sound. I think there is a HUGE benefit to having the boat close to home. Milford, Bridgeport (west of the main harbor) Stamford, Brandford, New Haven, West Haven, etc. etc. etc. are all nice places to boat.
Regarding your estimated costs - that's been beaten up enough already. A mooring can be much cheaper (for me it's $120 for the town permit, $100 for the mooring to be dropped in the spring and another $100 to be picked up in the fall), but, if you plan on spending weekends or longer on board, a mooring has no electric, water, or easy access to the showers, etc. on land.
IMHO, you should look for a Catalina 30 in decent condition. THere are millions of them all over the place. You should be able to find a nice one, ready to sail, for $30K. Buy it, sail it, have fun. If you love it and want a bigger boat you'll get your money back when you sell. If you hate it, you'll get your money back when you sell. If you decide you want to keep it, that's OK too.
Day To Remember, 1986 O'day 35 For Sale
Deep Blue C, 2002 C&C 110 For Sail
Mt. Sinai, NY
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