Re: Very n00b questions from a prospective sailor.
Therm, you mention being close to NYC. I have one of my trailerable sailboats at Spruce Run Reservoir near Clinton, NJ. It only cost me $295 to keep the boat rigged on the trailer at the boat launch for the sailing season. I can be launched and out on the lake in about 15 or 20 minutes. I have bigger long term goals than my current 16' and 22' boats, but I am just learning how to sail myself. There are some very affordable trailerable sailboats around, and you don't necessarily need a truck to tow and launch them.
As far as lessons go, my wife and I did a 4 day liveaboard ASA 101/103 course on the Chesapeake Bay this summer. It was awesome! Even my wife(who was scared of sailboats) had a great time. It was $750/person for the class and books, we stayed on the boat, and it included breakfast & lunch. It was worth every penny! I probably learned as much in those 4 days than I managed to teach myself by mistake in my entire first season. However, I went into the class with a basic understanding of sailboats that definitely helped. There are some very affordable options out there if you keep looking around.
1980 Compac 16
1983 Starwind 22 w/pop top
Trailer-sailing our way from Pennsylvania to Ontario Canada and soon the Chesapeake Bay!!!