I wear Redwing 2408s daily. Been my boot of choice for 10+ years now. I'm a field engineer in heavy civil / marine construction so I'm a mix of office / field work. Some days it's all office, some days it's 12hrs straight outside in all sorts of conditions (not a ton of winter, but I did wear them through 4 NYC area winters). Technically this is my third pair (I've had them resoled once or twice as well). I typically wear through the soles completely. Never had an issue with the uppers.
I typically don't wear waterproof boots. If it's going to be that wet, I switch to muck/rubber boots. Just my preference. I think waterproof boots make your feet hot and sweat more. I wouldn't go stand in 6" of water for hours, but if I'm just stomping around a muddy jobsite with puddles they are just fine.
The Red Wing uppers do take time to break in. I've been in my current pair in more of an office setting for about 2 months now and I think they are just starting to feel broken in.
On the flip side, I had a good friend/coworker who swore by his $60 walmart steel toes and just bought a new pair every 9-12 months (sometimes as little as 6) when they inevitably fell apart at inopportune times