So from what you've described I'd say you may want a good backpacking or backcountry hunting boot. It doesn't sound like you need a mountaineering boot (crampon compatible, synthetic contruction, etc). You could could find a light mountaineering boo very nice, they work very well for some folks. I've never used them so I don't have an opinion there.
What a backpacking boot will likely get you over your Redwings (and the degree to all of these will depend on the boot and which redwing). I would expect the backpacking boot to be stiffer to provide more support for your feet while carrying heavy loads, more weather resistant (less seams, a goretex liner), likely lighter weight, more grippy sole, better lacing system.
That said I've seen folks backpacking in cowboy boots and having a great time!