IMHO, if you want to split the difference, you'd be hard pressed to beat the value/quality/functional nexus of this boot that Herring sells. And don't forge you can get a 10% AAAC discount on it. Discount code: AAST
Allen Edmonds has a weather resistant version of their Higgins Mill boot design that can frequently be found of sale for something under $300. It looks good, is well made, water resistant and is fitted with a Dainite sole, providing pretty good traction. If you are going to depend on a single boot/shoe, this might just be your best option.
I have been wearing Gokey oxfords for the past year. Soon to have the soles replaced with vibram mini lug soles but they are functional, sturdy and wear well. Gokey was sold by Orvis to a private entity a couple of years ago and the shoe redesigned to accomodate an orthotic if you wish. It's my go to shoe for everyday wear in cooler/cold weather.