If you're single-handed you should probably stay inside. As always, the boat, the crew and especially the conditions will be the key decision factors, and only you (with perhaps input from the boat's owner) can decide. Another consideration is that if you're not familiar with this particular boat and its systems, when things break you will have many more options for safe anchoring
and assistance if you stay inside.
I haven't gone outside but have considered it. Having done the Delaware Bay & Cheaspeake route
I know it's going to cost you an extra day (Delaware Bay is forever and can be stinky in wind-against-current), so if weather
permits and you have adequate crew to run nonstop you should go outside. I've reviewed the charts
of the Atlantic-facing Delmarva inlets and it looks like they'd all be pretty dicey in the wrong weather
, with perhaps Ocean City (if memory serves) being the best option -- but without knowing it I wouldn't even try that one with the wind
in any easterly quadrant and/or adverse current
So IMHO the bottom line is go outside only if you're ready to commit to running the whole length of the Delmarva nonstop.