We've worked out a compromise

Since he is the one who wants to spend time with his family, he is driving up a week earlier. That way he gets his road trip (in his own car), and doesn't have to fly. He is between terms in school, so has time to spare. That gives him more time with Grandma, who is getting on in years.

I will fly up a week later, he will meet me in Boston and we'll drive up to his place. Then, in two weeks, he'll drive back, dropping me off in Boston on the way back for my flight so I can be home in time to go to work the next day.

Airfare runs about $210 from JAX to BOS, so that will work. THanks for all the help and suggestions !!!

Now I just gotta figure out where we should do lunch when I get to Boston...?