How bad are the winters north of Boston/how much driving do you typically do and where? I spent some years in Boston and with quattro I would think you would be able to get by with some good all season snows (I'd recommend Extreme Contact DWS).
Had a TT for sometime and was able to get by on whatever the factory tires were. Mind you the TT doesn't even have legit quattro (haldex shared with the R32) and I was perfectly fine.. Driving cautiously obviously. I would also look into any used tire options.. Big fan of Nokians myself.. If you can find a set of used Nokian winter tires I'm sure you will be very pleased.