You don't really need the radar or AIS to sail at night on the Bay. Very few have AIS and very few use the radar a lot on the Bay. I have both and rarely use except in fog or at night when in a shipping area to identify a boat. For the most part I am not in shipping lanes.
James you certainly can do the RI trip easily. You've gained a great deal of experience doing the Delmarva, but could have done the coastal stuff as well. I have followed your trips closely and picked up a few pointers/ tips from them.
Anyone can really sail up the coast. 20 years ago when I lived in south NJ and we went up to MV or the LI Sound there was no on board electronics to speak of compared to today and it all was done with compass, dead reckoning, paper charts etc. You still should be able to do it with this method in spite of having the new found electronics IMHO
RI is my next trip. I have done the Delmarva coast 4 times, 3 time solo and I do not have radar or AIS or a life raft or lines led aft or a $300 harness, or any of the totally unnecessary and expensive convenience items recommended by some of the members here (some of whom have never left the Bay). Nor will I likely buy any of them.
While I appreciate your opinions and traditional sailing viewpoint here, and have done this trip sans the stuff above, I would say that the word unnecessary is not the word I would use to describe them.
Having been caught in thick fog for 2 days which is common in RI, I would tell you radar is comforting to have. Having done NYC at night it is the same. Lines led back, life raft Radar, AIS, are not " essential" items, however I would not characterize them as convenience items either.
Sailing at night or along the coast may be a little riskier in some senses so I look at them as helping with risk avoidance. For instance it is less risky to have radar on a foggy night or a night crossing shipping lanes of New York harbor than not. It is less risky to be able to put your sails up, reef or douse from the cockpit than going above when single handing. The equipment is non essential, but helpful.
You can get from here to Florida without air-conditioning in your car. Air conditioning is a convenience and may keep you fresher and more alert, but it isn't a necessity.
Everyone chooses what you want as far ask risk minimizers and avoidance and conveniences. To term them unnecessary isn't useful. It doesn't make you a better sailor whether you have them or not. It also shouldn't deter you from trying new adventures.
Also and somewhat importantly my wife sails on our trips too and has the helm about 1/3 of the time and some of the conveniences make her more comfortable in "captaining" the boat from the helm. It is essential to keep her happy and comfortable and free of fears.
Of all the electronic conveniences I have added I would say radar and the Chart plotter in conjunction with prior techniques and knowledge have helped with safety. Should they get knocked out...I will easily survive....but like air conditioning...why just survive