Hiring a good delivery skipper to go with you and give you the benefit of his knowledge might be the way to go. I can't do it as I'm booked, so I'm not angling for a job, just dispensing free advice.
Philosophically, you need to remember that your boat is small and the sea is big. Go at this very humbly, I notice a bit of the kind of arrogance that gets people in trouble in some of the comments on routes.
The weather still can get very snotty very quickly that time of year, and the water is still very cold. So watch the weather, don't be in a hurry, and be prepared and make sure your crew is prepared to sit at the dock and wait for better weather.
If you want the more direct route, pick a nice SWly to leave on; one that is going to last a couple of days, at least, and head up toward C May or Atlantic City.
Don't try Barnegat; it's tricky and it's not worth the risk. Out of many dozens of trips up and down the NJ shore, I've only gone in there when I was dropping a boat there. It's only 53 miles from Atlantic City to Manasquan; you should be able to pick a weather window that long.
As for going up the Chesapeake, it adds only 50 miles to the trip, and it's a good way to shake down the boat and the crew.
Before you leave, learn what lights mean, both ship and shore.
Winds are generally westerly that time of year, so going up the beach is a good option. If you stay in 40 feet or so, you should have a nice flat-water ride no matter how hard the wind is blowing. Careful of the reefs going up the DelMarVa shore. Bear in mind that if the forecast is for NW winds, you will have wind and waves right on your nose and get no lee from the land.
Again, in many years of taking this route, 75% of the time I end up going up the beach and down LI Sound. The offshore route can be a pain weather-wise, but also the traffic is horrendous with ships and fishing boats all trying to run you over...or so it seems. Mid May is pretty foggy offshore, so you can imagine how much fun that will be, no matter how overloaded with electronics you are. My advice is to not take the chance. And going through NYC is enthralling and adds little to the mileage.
For a brief take on how to find a delivery skipper:
Yacht and Delivery Captains: A Wealth of Knowledge and Experience « « www.yachtworld.com www.yachtworld.com