Guys, thanks so much for all the responses, this is great information. I was completely clueless about where to moor the boat around NYC. Now I will start to call around to check out mooring prices.
I am also going to expand the search to slightly larger cruisers of the following type,
1. Sabre 28 - My first choice. Hard to find good cheaper examples.
2. Pearson 28 - The girlfriend loves the interiors. Don't seem to be many around for less than 20k
3. C&C 27 - Really like these and I've heard they are fast. I've seen a couple of these priced around 15k, one with outboard and racing sails, another with an inboard diesel.
4. Catalina 27 / 28 - Looks like a lot of boat for the money.
5. O'Day 28.
Newport 28 ? Don't know much about these and I've heard the C&C is overall a better choice.
I would include Cape Dory 28 and Tartan 27 but the lines do nothing for the lady.