I recently moved aboard and highly recomend it. For me it was much slower... about 3 years since I started thinking about it. But in that time I learned to sail (I only knew very basic stuff before that), and learned how to work on various boat systems while not being completely dependent on them. Looking back, I think it would have been difficult, but not impossible, to jump into it all at once.
My actual move was not easy. I moved out of my appartment on the last day of the month, rented a car, picked up my delivery crew, and headed to Maryland to deliver my new boat to New York. I had owned the boat for about a month and spent 4 weekends working to get her ready for the delivery. That only left weeknights after work to clean out my appartment which was not easy.
So start getting rid of you stuff now! With 2 people on a 28 footer, you really wont be able to bring anything, but thats part of the beauty of it. Still, I would consider bigger boats, say 30-33' and wide beam, if possible.
Western Long Island Sound