I go on a multi-day backpacking trip each year where we usually cover 25-30 miles each time. I've been wearing the same pair of Asolos for the last 200-250 miles, and my next pair (if this pair ever wears out) will be Asolos, too. They're light, super comfortable, and required very little break-in.
Regarding getting your feet wet, as another poster suggested don't try to keep your feet dry (or expect that you will). Wear a good, breathable boot and a proper hiking sock that wicks moisture and you'll hike your wet boots dry. For socks, I'm partial to Smartwool based on great past experience with them.
Both the boots and the socks can be found at REI, but neither is cheap. Boots are $170 or so, and the socks run about $25/pair. Keep in mind that proper gear lasts a long time, though, so you'll be enjoying it for years before you'd ever need to replace it.