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To follow up on boasting, why would the players ever not out boast each other for double the bonus? It seems like there is not downside to out-boasting fellow party members. Additionally, is the benefit gained while pursuing the boast, or after completing it?

Apologies for the very late reply. 
Boast benefits are immediate. 

The out-boasting is meant to be more collaborative than competitive. Players could game the system, but I would just ask them not to. I find writing rules "defensively" gives very bad results. 
 Being able to out-boast is something that NPCs can do too. The idea being you can egg someone on to taking on a too-large Boast, and getting themselves killed.