Sounds like quite a transitional time for you, I'm not surprised you feel like your head is going to explode. I like the idea of a month off - how would you feel about doing that? After all your finals it might be nice to chill for a while.
I went to Boston and loved it; it was one of my favourite cities. It has such a different feel to NY. Do what is right for you - and Boston to NY is not that far really.
You did such a good job with B and were great at not pressurising. I think he responded well too so I think you can give that a big tick as having worked!
P.S - when I think of Virginia I automatically think 'The Waltons'. I *loved* that programme!