WK99 good logic. Will note have done the C&D/Delaware more times than digits. Very boring except on one occasion a barge with metal scraps caught fire. Apparently those fires burn so hot water can’t be used but only foam. Find the trick for the Delaware is to stay as far as you safely can away from the shipping channel. There’s a couple of good places to anchor on the Delaware side just before the canal and you can anchor in spots along the sides but it’s fairly open. Okay if wind/wave direction allows you to anchor in the lee of the land. Otherwise just struggle through to cape may. Have found cape may quiet regardless of what’s going on outside. Truly a harbor of refuge. Like to anchor near the CG station to get a jump on doing the NJ coast.
Wife prefers traveling during the day and there can be debris in the C&D so try to go from chessie near canal entrance to CM in mostly daylight. Again will time for currents but wonder if OPs boat could do it. There’s fuel in the C&D and CM but don’t know if available elsewhere on this leg.
Another concern I see for the OP is range. It means he needs longer weather windows or more time waiting for one. Recently have taken to topping off before leaving the chessie. Have no concerns doing NJ coast at night. So damn the fuel bill and go top of chessie to Atlantic High lands non stop. Then after resting for a day or two AHL to western LIS. Then another stop followed by run to either Sag Harbor or port Judith. Then New England. Only stop in marinas for fuel and pump out. He will need more fuel stops and shorter legs.