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It's about boots, it's about socks, it's about insoles.
The Redwing Burnside boots are MIGHTY comfortable just right out of the box. But the soles are on the soft side, they won't last much over 2 years of hard labor. They can be replaced with I think it's the Montana vibram sole for $100; it's compatible but also harder. So...bonus.
It's hard to beat the socks at Buffalo Wool Co! Buffalo wool socks breathe well, and they're tough, too. They wear very very slowly. Don't hold an odor. Have adequate cushion.
When the regular insoles of the boots wear too thin, it's time to switch over to SuperFeet insoles! I get the 'Orange' ones.
That combination should get you some very comfortable, high quality boots.
Food for thought, my military minded friends talk about jungle "Mickies". I think. They say you will hurt & blister breaking them in over a few months, but then it's a very comfortable pair of boots that last a long time. And they're pretty cheap, too. I'll talk to them again & update my post with relevant info.