What and how should I look for when choosing a pair of good hiking shoes?
I need a pair that keeps water out and that I can wear both when hiking and through cities (so I don't need to carry another pair).
I'm not looking for a specific brand (although some examples would be welcome), but rather - how do I test whether it's waterproof (before I buy it), how do I know it will be comfortable (I hiked for a day with a pair I got from a friend - they seemed comfortable at first, but then it got really bad - so bad that I lost a toenail after a few days)?
And also - what else should I look for (besides waterproof and comfortable)?