Congrats on your imminent purchase! Both Connecticut and Rhode Island can be great places for boating, and any berthing selection you make will involve trade-offs in many different ways.
A couple of years ago, we had a mooring in Eastern CT (Avery Point) and found the longer commute (about an hour for us in moderate traffic, much longer in heavy traffic, especially on late Sunday afternoons) was a real challenge for us. We didn't have as much flexibility in our schedule back then which could have helped mitigate the travel time problem. In contrast, our current mooring in the CT River is about 15 minutes from the house and Rt-9 is rarely over-congested (unlike I-95), so that convenience and predictability is very handy and enables me to get down to the boat more often during the week too!!
Another aspect to consider is the predicted 'quality' of the slip/mooring you're considering if you are thinking about working/sleeping aboard quite a bit. In our experience in Eastern CT, the mooring was heavy tackle which was somewhat exposed to the SW, and on brisk days (or nights), the area of the mooring field I was in could get pretty rough for working/sleeping aboard. The rollers from the ferries would come through pretty regularly also (and sometimes right on the beam when the wind was S - ouch). In contrast, we have very good shelter on the CT river which is nice, especially when it's blowing hard (and is more comfortable to be aboard in a wider range of conditions). Smoother water has got to be easier on the boat (generally), I would think.
On the plus side, though, the water is much cleaner in Eastern LI Sound and RI Sound, so that's a key benefit of going East, and the one thing we miss the most I'd say (although the CT River is doing better these days, it seems). The sailing is also better out there too (especially in RI, to your point), so if you've got the flexibility in your schedule and can find a reasonably sheltered location, you may want to take a look at a few RI alternatives (and just talking about it reminds me that we're due for a trip out to Newport).
Last edited by rwy36; 08-02-2011 at 11:15 PM.