Maybe it depends on how competitive you intend to be. I've raced the past three seasons with a pair of $80 Pearl Izumis (Quest, I think...whatever the Select replaced) with mesh and leather uppers and three velcro straps. I had to take them to a cobbler because I keep doing something that cuts the inside of the right heel open, but other than that I have no complaints. I've seen people have trouble unbuckling their shoes after a particularly muddy race, but I haven't had any problems with the Velcro straps.
I can't imagine any shoe that's going to keep your feet dry. My recommendation is to wear thick wool socks.