The test in NH is $300.00 two days rideing and you ride 500cc Buel Blasts, Mike has the right idea. My youngest will be taking it when she is done collage in May.
He's going to be riding in the snow??? You wont get too much motorcycle for 3 grand period. A shadow isn't a bad starter bike but to expect to use it as his only transportation in a winter state (I live in NH) is not practical.