I have no experience with the R23. I have owned a 2012 R27 for eight years.
If your R23 is like my R27, the problem I see with trying to live on the boat in the winter is that there is no insulation in the boat whatsoever and air gap leaks galore. Consequently, whatever you use for heat will run nearly constantly to maintain a comfortable temperature. It’s very much like a car in that respect. What happens when you shut off your car in winter cold? The interior gets cold, fast. Your boat will be exactly like that.
Condensation inside the cabin will be a constant problem. Remember what happens in your occupied car in cold weather with the engine shut off? The windows steam up. The same will happen in your boat, except worse. The warm moist cabin air rising to the uninsulated glass of the overhead hatches will condense and then drip back down. This will happen CONSTANTLY whenever the boat is occupied.
You also need to think about how you will get water to the boat. If you are going to use a hose, whatever spigot you use will have to be frost-free. And during periods of below freezing temperatures, the hose will have to be drained after every use. And if severe cold weather hits and there is a power outage, your boat plumbing will suffer catastrophic freeze damage unless you have a back-up generator capable of powering whatever you use for heat.
Are you also going to take care of personal hygiene in the boat? If so, that 22 gallon fresh water tank will need constant refilling. The 11 gallon waste holding tank will need to be pumped out every few days.
As cozy as your boat seems now, it won’t be in the dead of a Massachusetts winter.