The redwing's tend to be bulkier in the toe due to the larger toe box. The wolverines have a more dress-shoe type of toe. The 1000 mile boots tend to be more comfortable due to their lightweight construction and thinner leather. As such, I've heard the 1000 miles tend to be more comfortable for this very reason, especially during break-in.
I'm looking for a casual boot that I can wear EVERY day that can also be dressed up for nights out. I'm scrapping every other shoe I own except a pair of workout shoes and my dress shoe collection.
I like the RW's over the 1000 miles for these reasons:
*rubber soles, prevents slipping and leather soles from wear/splitting
*more manly appearance (This is a big one for me!) No man should wear a pair of shoes that can be confused with your womans'