Never ever sneakers. On dress shoos I use for humping around the city I apply the rubber covers, which is good in wet weather and takes forever to wear out.

^ Depends on the quality of course, but crepe goes faster than leather.
Crepe soles are usually a bit thicker though, so they have about the same mileage.

Provided they are welted, yes they can be resoled. Without ripping.

I have a pair of Alden boots with "commando" soles. They're great in the snow. My Indy boots with the smooth sole are fine for 'skiiing' ( I've actually rode down a tobagganing hill on them (while standing!- and much to the consternation of the other dads on the hill )

Perhaps it should pain me to admit this, but if you lump very casual "weekender" shoes like the Allen-Edmonds Wilbert with rubber-soled "dress casual" shoes like the A-E Ashtons that are gracing my feet at the moment, I actually wear rubber-soled shoes more often than I do leather-soled. However, I wear leather-soled shoes to work more often than anything else.

Perhaps I can achieve a degree of forgiveness and redemption when I mention that the only time I wear sneakers is when I am working out.

I have a pair of chukka boots with dainite soles and a pair of black shoes with that thin rubber sole Edward Green use (is it Thames?) that is the same thickness as a normal leather sole for when it is wet out.

I have problems with vibram soles because snow gets packed under them and I wind up involuntarily imitating Yatchie's 'skiing' but with rather less dignity I suspect!