Boots - Rocky or Danners
Between the 2 Danner gets my nod. I have had a few pairs from hikers to cold weather. Their service is second to none in my book.
I will add I also own Russell Moccasins Grand Slam sheep hunters, South 40's and Cabela's Meindl hikers and use them all the time.
They all have their purpose. Kind of like Navin
There are a lot of factors already mentioned, but you need to find a boot that fits your feet for starters. Danners fit me great and most have a zero break in period. The boots made in the US are better, but also more money. Usually through the grouse season, I will wear out a pair of boots with 8-12 mile days. Right now I think I own 4 sets of danners and 1 pair of irish setters. The Irish setter have held up better (kangaroo leather), but don't fit my feet as well and my ankle rolls easily in them. The danners are like slippers to my feet. As far as waterproofness, expect 1-2 years of heavy use. That has been my experience.