@Justin Tadlock -
He should strive to be unbiased and impartial and report events etc. If he wants to be one sided he should write something on a about page that he most of the time goes the official party line. In Sweden newspapers declares themselves liberal, socialist etc so you can interpret the editorials accordingly.
Especially now that hes gone commercial really. To increase the brand WPTaverns value and his own reputation I think it would be beneficial to remain impartial when reporting events and then have editorial pieces where he speaks his mind. He might not get as much freebies from Matt but his own value will increase?
The WPTavern is popular and I'd like it to become even better and better since it really is a great resource most of the time.

Speaking out against the core team’s decisions doesn’t make you an outcast or anything like that in the community.
Probably depends on the decisions in question as with the whole GPL debacle =). And if you have any popularity to begin with.