We lived aboard for awhile at the Galley Store for a few months before transferring to Morehead City. Having stayed at both Bridgepointe and what is now called the Grand, we much preferred it. In the nicest part of town with a great little store on site and good restaurant, fule dock and in the larger slips in-slip pumpout. Much nicer docks and better electrical than the Grand in particular, with much better views. Our second choice would be the newly refurbished Bridgepointe for quality of docks, a short walk into town via the bridge.
But , like others, I don't get the OP's in-out-in strategy at all. My first reaction is, why not take the boat to New York and the primo cruising grounds attached thereto? We looked forward to our northern summer journeys more than our southern winter ones (personal preferences, I know). Or at the very least somewhere on the Chesapeake where it can be cruised indefinitely all summer. We live in new Bern now, and have owned property there since 2005, and it would never occur to me again to keep a cruising boat there for any length of time.
Secondly, when we stopped full time cruising, we soon relocated to Morehead City, with better access to the fabulous beaches and the best "stay awhile" anchorage on the East Coast, Cape Lookout Bight. Also very accessible to the cruising grounds on Pamlico and Albemarle sounds, and points south via the Atlantic Ocean and ICW. So if there is some unusual reason that the boat can't go north for the prime months, I'd look at that area myself without a moment's hesitancy. Some marinas require the boat leave during a named storm, but there are plenty of captain services and boat yards that can help with that through prior arrangement.
"There's the Right Way, the Wrong Way, and what some guy says he's gotten away with"