STOP IT!!! You're over-thinking(agonizing) this thing. I've read your previous posts, and i think your more than capable. Being cautious is something you should have , just for a day sail.
If you buddy boat, you may be following someone with questionable judgement. Do your own planning, use your own gut instinct, but don't follow.
Current and wind are the main things for Del. Bay. I usually try to leave the mouth of the C&D about 1-2 hours before high tide or slack current. It's a little slower at the beginning of the trip, but the current will be with you the rest of the way. At that time of year, plan on motoring the whole way, but you may get lucky and be able to motor-sail.
When your heading back, you may just enjoy one of the best sails you've ever had.
Don't be on a schedule, plan well, and go for it.