I'm toward the radical end of things, I suppose, since I have converted to Nike Free Trails 5.0. They have a lot less structure than most trail runners. I weigh about 210, so I give any shoe a workout. I get higher daily mileage with greater comfort with the Nikes. I do not stick to trails, but go cross-country a good bit. I have never turned or sprained an ankle, partly, I think, becauce the Nikes tend to strengthen ankles and improve balance -- radically. I am constantly amazed at the difference this makes.
Regarding water, it depends on the situation. In cold weather on a wet trail I wear w/b socks or sometimes neopreme socks. In moderate weather, I don't worry about getting wet. Getting feet wet is dangerous only below freezing. or if you cannot get them dry and warm for a few hours every night - which could result in chillblanes.
Waterproof boots? Nothing is waterproof. Such boots get wet and take forever to dry and weigh twice as much until they dry. If you really want to keep your feet dry, use two pairs of waterproof socks on each foot. Put on a liner sock, a waterproof sock, a wool sock, then another waterproof sock. The wool stays dry that way. Change the liners periodically. Then, it does not matter what shoe you wear, but something that does not gain a lot of weight when wet and dries quickly is obviously the better choice.
A word of warning about ankle supports - whether they are in fhe form of hinged braces or 'supportive' boots. It is accurate to think of them as a glass cast. Up to a point, they will prevent your ankles and musculature from working properly. The consequence is atrophy - weakness. When the supports fail, as they will inevitably do, they will fail catastrophically. And so will your ankle.