Michael, thanks for the clarification and the dropbox link. The picutes look great! Big thanks. And I read John's Lug Nut article before...it's a cup of koolaid that I'm pretty willing to drink.
To "No inexpensive launch points with easy access to open water here in Coastal Connecticut. Out of towners pay dearly for living inland.",
I also love the idea of a southern NE meet up. I may be meeting up with a shell of a boat only, but like you I am building my wife an art studio (that makes my shop look like a playhouse) and it's really getting in the way of my own project(s), I won't even mention my 4 month old. She can't get anything done by herself...kids these days.
Two launches that I love using in CT are Brandfords town launch (free) and Guilfords (really cheap). Also, although this may be too far of a hike for you, Rhode Island has so many free awesome launches.
As far as the CT river goes, I'm really hoping to explore it more this summer. I live about 2 miles from a ramp in the Pioneer Valley, but it's $20 to launch.
BUT
There is a free launch in Hatfield and one in Northapton, both on the west side of the river. Both ramps are fine enough and parking is usually not an issue. Out of the two, Hatfield would make for better sailing. But I personally would turn the car south and head to Guilford.
Tim