If you had three pair of well-made leather shoes, you could potentially keep them for decades by not wearing the same shoes on consecutive days and treating the leather every few months.
I'm a fan of low leather boots. Good looking low leather boots can be worn in just about every situation except weddings, and last a hell of a long time. It's rather liberating not having to worry about your shoes before deciding to walk through a soggy looking field or climb up a hill.
I've given the south west some thought, though it seems the north west is in my immediate future. Should definitely be an improvement over the east coast at least.