I'm missing something in your math. How is $168 (+ rental car and gas) < $130? Unless you're somehow factoring the cost of your time into the equation? And ignoring potential ridesharing from Boston?
I frequently look for cheap flights to Rochester; beware of the cheap flight that is not direct, because then you're losing the same amount of time.
My car can do that round trip for $100 in gas. Once you add a second person in the car, driving becomes a clear win. The second (or third, or fourth) person basically travels for free.
What time is the flight and when?
My guess, by the way, is that he is figuring in the cost of his time; 16 hours all alone in a car could be considered to have a pretty high negative cost by some.
I dislike long car rides, particularly before and after races. My legs tend to suffer; while the flight takes a bit more time than the 1 hour flight time, it definitely takes less than 8 hours each way. Some of the extra time is also spent walking around and moving, rather than cooped up in a car.
Put another way, the extra cost from plane ticket and rental car (especially split 2-3 ways) might be worth it to avoid the extra time from traveling by car. Your results may vary.
@Alex: because JetBlue and US Airways compete on BOS-BUF, it's usually far cheaper than BOS-ROC (on which US Airways has the only nonstops).
I dislike long (...er, most) car rides enough, and like Ian enough, that I would gladly contribute to a "fly and drive" fund for Ian. I'm not sure what I would contribute, aside from encouragement, but I would find something.