I guess it is down to the size or shape of your foot, but I find the regular sk8 hi are much more comfortable than the sk8 hi pro, which feels big to start with and blows out in the pairs I have had. I have a pretty solid rotation of sk8 hi or old skool, not so often wearing eras and a few others like half cabs and even authentics nowdays.
I do strip out the inner of most regular versions and put a nice comfy pro type insole in which gives me the best of both worlds, but the full suede old skool pro is a winner when I can find them.
It also depends on how you lace the shoes up too, because tight sk8 hi shoes don't give your ankle much movement and I found some things felt really strange in the sk8 hi, compared to era or old skools.