I've driven all those routes, not at the same time, but been on them one time or another.
I'm originally from Laurel Del, just north of Salisbury Md. Spent most of my youth trying to get out of that area, and wish I could afford to move back.
I was at the beach....(during the summer, of course) all the time, mostly OC. I usually go up there in Sep for the Dalmarva Bike week held lie the second week in Sept.
And yes, the Bay Bridge can be tricky on a bike. Hell, I remember crossing the Bay Bridge/Tunnel whjen it was just a two laner.....that was fun. Still is in the tunnels.