Followup:
After spending what seemed like half a day in Boot World trying on every boot in the store, I finally settled on a more expensive pair of Timberland Pro boots than I had started with. It is amazing how much more comfort that extra $60 will buy.
These things are really just as comfortable as my old hiking boots, but will definately outlast them.
These are the ones I got:
I must admit that I was surprised to see no one step up and suggest the old classic for painters - the white low-top Converse All Stars. Back in the 70's and 80's it was hard to find a painter that didn't wear them... not exactly what I'd consider the pinnacle of comfort though.
Anyway, my thanks to all for the insightful input.