Definitely try a bunch on to see what fits you, and make sure you wear the socks you'll wear hiking (and here's another recommendation for the double socks--a thin synthetic liner with a thicker wool sock over it; I use this system and have never had a blister from hiking). You don't want them too tight or too short, but you don't want your feet sliding around in them either--that can cause blisters. The size of boot that fits you may be a bigger size than you wear for regular shoes, because of the thick socks; my boots are an 8 1/2 when normally I wear a 6 1/2!! Waterproof is a very good thing! I can't tell you how many puddles I've stepped in or unexpected stream crossings I've had when there's recently been a lot of rain, and soaked socks are really the pits! As for places where good deals can be found once you know what fits you, check www.campmor.com and www.sierratradingpost.com. I got my boots (Vasque Picacho) from Sierra Trading Post for about 40% of the regular price. Happy trails!