On the other hand, I'm from the school of loving big boots and carelessly careening through, well, anything

For hiking, I have an old pair of all-leather Merrell's that have treated me fairly well ... originally I had some issues with width, but over time they've broken in well. I use these summer & winter with good results.

I had planned on replacing them earlier this year, potentially with something a little lighter (my Merrell's have a thick-ish lining) and that would treat me better on the declines, but wasn't able to find anything that fit well enough. Maybe I'll start looking again next year, but at this stage I'm unwilling to move to a pair of boots that doesn't fit me relatively well from the get-go (width is usually my issue).

Even around town I prefer to wear leather combat-style boots pretty much year round.