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.
You didn't specify a budget, but it looks like you are trying to stay under $20k. At that level, you should certainly be able to find a late 70s early 80s 27-30 footer in decent shape. The list you have is good. I would add boats like the Cal 28-2 and 31, the ODay 30, the Pearson 30, and Tartan 30 to the list. With any boat of that age, condition is everything, so the challenge will be finding something within your budget that you like and has no major issues. At a given price level, the smaller boats are likely to be newer and in better shape than the larger ones.
And CalebD, yes I am a member of the Hempstead Harbour Club in Club in Glen Cove. Thanks for your kind words about us.