Boots are a big deal to me. If my feet hurt it makes the rest of the trip miserable. The fit is the most important and I tend to have slip in the heels of most boots thanks to a normal fore foot and a narrow heel. The best boot that I have found for me and my narrow heels are the Lowa Rangers. They will cost you 50.00 more than you are wanting to spend but will last you several years or more. Refer to the below link for Baker shoes out of Oregon. Great company and they offer free shipping on orders over 80.00. I have owned a lot of boots (ask my wife!)trying to find some that really fit and the Lowas are worth every penny.
http://www.bakershoe.com/shop-by-brand.cfm/brand/lowa-boots/product/lowa-ranger-gtx/ 
