I think it's important to know what problem you're trying to solve by replacing your shoes with boots.
Boots vs Shoes
With boots, you get some ankle support and protection. But, you gain significant weight on your feet where weight is more significant. By providing ankle support, boots also reduce ankle mobility. This can affect traction on some surfaces and how your leg muscles are used (some are used more and others are used less than with shoes).
If the problem is that your feet are less stable in shoes, one option is to go the other direction and use shoes which are even more minimal, such as lighter/flatter running shoes ("flats"), or even Vibram Five Fingers. These can cause other issues though, and might not be well-suited for the terrain you hike in.
Another option is to see if using a pair of trekking poles helps.
Waterproof vs Not
I think it's best to have non-waterproof footwear. If the trail is fairly dry, it's nice to have non-waterproof footwear. If things are so wet that your feet will stay wet, it's often better to have waterproofing because sweat wets the socks slower than water or rain from the trail. This is especially true if the temps are cooler (< 60 F or so) The only practical way to have this situational adaptability is to have a pair of waterproof breathable socks. Also, leaks in socks are easy to find and seal at home compared to leaks in footwear.
One issue with wet feet is sock thickness. Very thin nylon or polyester socks (such as running socks or dress socks) will dry much more quickly than thicker socks. But in the cold, thicker wool socks are often needed to retain warmth when wet.
I currently have non-waterproof hiking shoes and all-leather GoreTex-lined boots (Salomon). I haven't worn the boots in a year or two, and then only on 2-5 hour day hikes in colder, wet weather. In wet conditions, the boots keep my feet much drier than if I were not wearing waterproof footwear. I don't think they leak, it's just that they're limited in how breathable they are. I suspect the GoreTex liner has survived unpunctured because they're all leather. I plan to get a pair of GoreTex socks to use instead.
Edited by ohiohiker (09/11/10 11:19 PM)