I'm very budget-minded, so I generally will book a lower-priced property on the edge of town rather than a nice, centrally-located property. With the free night award, I'd still feel like I was "overpaying" by booking the latter, especially since I'd probably stay more than one night (covering the next with points or cash).
Where is there no other option, or where is that other option a pain (like, an hour out), or where does the quality blow the budget options out of the water, or where is being in a prime location REALLY worth it?
I'm thinking beachfront, or a city with bad traffic, or a city with not-so-great neighborhoods... any specific suggestions?
Focusing on US, but will take suggestions for Canada or Western and Central Europe.