As far cracking, everything after the 1999s crack. This is especially true with the 2003-2010 pairs. The more recent pairs still crack, but it takes a lot and isn't as pronounced. My Mars Blackman 4s and my fire red 3s from 2006 cracked under 4 wears.
From the looks of these, cracking should not be an issue for a while. All of the post 1999 3s and 4s are painted, while everything pre-2000 looked like they were sprayed on.
With the fit, these are tts. They are leather, so they will eventually loosen up. Don't go up a size if you don't want to eventual boat shoe feel..