Reb...my bad...I was thinking Legend 375 not Cherubini which are much better built and should be up to the task if well maintained/upgraded as yours sounds it is. 6 aboard for that trip should be interesting!
Just for your "alternate" thinking...pulling in at Beaufort and heading up the ICW to Norfolk will take 3 days. You can go out of Norfolk to Montauk and CT in 3 more days.
Your plans for the radar/chartplotter as a "nice to have" addition to your redundant "must have" equipment is exactly reflective of my own view.
No longer posting. Reach me by PM!