I had a pair of Redwings last year for a little over a year. They were very waterproof up until the end. I bought a new pair this year and they're going back. Dang things leak and they're only 3 months old.
I will say that I have a pair of Bates Swat/combat boots, side zip for maybe 2 years. I wear them most of the time when I'm not working, for everything from going to the store to hiking all day. They're extremely comfortable and the waterproof lining is still working over a year after the guarantee. I do a lot of outdoor photography and I can stand in small creeks looking for the perfect waterfall shot and my feet are dry.