It looks like you are based in Stoughton, so I think that you will find warmer water much earlier if you look at the south facing areas of Mass. South facing beaches on Cape Cod, Buzzards Bay, Westport etc. I've paddled one day in Hingham and the next in Buzzards Bay and found water close to 10 degrees warmer. Regarding clothing, I think that drysuits are worth every penny you pay for them. And a drytop is also versatile and can work with a farmer john. Check out immersion research's outlet page, they often have 2nds or samples.