Came here for nose and tail discussion, but I'll share my shoes methodology. I keep two pairs of skate shoes. One that im currently skating with, and one that is my daily casual shoe, since they fit my style anyway. Once I break through the sole on skate pair, I get a new set of dailies and rotate the former dailies to skate duty. This way I start with somewhat broken in shoes for skating, and can rotate my daily shoe style instead of wearing the same shoe style for many years.
Even then, the first few sessions I'll wonder if I can ever skate the new shoes because they feel weird, but by session three they become my new favorite shoe of all time, without fail. Weird mental gymnastics.
Edit: the old skate shoes become garden shoes, try not to waste