As planners we are usually more progressive than non-planners, at least in terms of land use, transportation issues, and the like. What do you think is a better career choice or will benefit the most people: going to a non-progressive town and trying to adjust the usual thinking they have or going to a more progressive town where most people already buy-in to it.
For example, if you want growth boundaries, mass transit, and mixed use, moving to Portland is great. However, you personally may make little difference because what you want they already have - you're just another fish in the sea. On the other hand, if you moved to a more suburban small town would you have more influence since you theoretically have more power? Ultimately, where do you think you could do the most good?