I have been sailing on Long Island Sound out of Glen Cove for the last 30 years. I had sailed an Oday 22 on Barnegat Bay NY and traded up to a Pearson 26 when I moved to Glen Cove. As well as daysailing and club racing, my wife and I cruised that boat as far as Cape Cod and the Vineyard. In 1989, we traded the Pearson in on a Cal 9.2. The 9.2 has been a great boat for us - quick and lively to sail but with reasonable cruising accomodations for a couple. We now have our 9.2 on the market so we can move up to our "last" boat, something in the 33-35 foot range.
Since most of your time is spent daysailing, I think sailing performance is most important. And light air performance is essential if you are going to enjoy the typical days in July and August. Getting that plus comfortable accomodations for 4 adults in a 24-30 foot boat is not easy. A boat like a Catalina 30 will give you decent cruising accomodations, but won't perform like my Cal 9.2 or a J30 or a Pearson Flyer.