For me I think part of the reason I'm so very very quick to commit to one boxing is the low improvement in outcomes from 2 boxing as the problem was presented on the wiki.

The wiki lists 1000 vs 1000,000.

If I was sitting across from Derren Brown or similar skilled street magician I'd say there's much more than a 1 in a thousand chance that he'd predict that I'd one box.

If the problem was stated with a lesser difference, say 1000 vs 5000 I might 2 box in part because a certain payoff is worth more to me than an uncertain one even if the expected return on the gamble is marginally higher.