Quote from @Patrick McCann:
Quote from @Nick Maynard:
Hey Nick, were you able to get in contact with anyone and were they helpful at all in the situation?
Hey Patrick, I actually ended up just meeting with my town's code enforcement officer and confirming everything with him. 3 other people in my town have used this program so far to build separate houses on their lots, so he had some experience with seeing the process through. As long as the new house meets all of the town's zoning requirements, he said that we could indeed build a second house on the lot and it would be treated essentially as a condo. We could sell that house by itself, but it would be sold under a land in common agreement and an HOA would need to be formed.
I also confirmed with the Public Works department that a 2nd driveway can go in, with a septic designer that there's room for second septic tank, and with the public water company that they can tap into the main water line from one of the neighboring roads.
I'm sure there are some more details that I would need to iron out that the code officer didn't bring up, but the high level answer I was looking for is that my town does allow selling off a second house under the LD 2003 legislation.