I tend to think Tobin does best when I'm driving and Matt sits in the back with him. We've been able to drive rather long stretches, especially when I'm driving: sometimes as many as 4 hours without stopping. For one thing, Matt is more entertaining than me in general. :) And I think Tobin is more likely to want me to hold him when I'm just sitting there right beside him. It's not that he doesn't want Matt to pick him up, but more about the relationships we've developed with him as parents. Mama is the primary nurturer. Dad is the primary playmate and, I would contend, teacher.
Tobin was also pretty much perfect when I had to fly alone with him to Kentucky (Matt had driven up a couple of days before with Hannah). He slept for the entire flight and only displayed a little crankiness when I had to wake him to get off the plane.
Tobin's good-natured traveling is really so symbolic of his general attitude towards life. He's a happy kid, who takes most things in stride. And we're so thankful for him.