Wow, I'd been thinking the little guy would prefer to be up close to me, in the child seat on my bicycle. But now I see the benefits of using a trailer. I hadn't thought of him being able to have the entertainment of toys, books, snacks, etc. in the trailer. We used to have a trailer, years ago, when our kids were small, and it zipped all the way closed, with a screen front. Great idea. I'll have to do some shopping.
I also like the idea of not having the child seat on the bicycle for long rides. Then I can pack my bike the way I usually do. I have a BOB trailer and the hitch works fine on my bike even with the rack/panniers I have. A Burley should work okay too.
The food bribery and stopping more often are good ideas too. I hadn't thought how long 2 hours would seem to a child that small.