In regards to the cup/vulc question: Right around the time I started to notice that my feet would hurt after skating with bad shoes, I tried some PJ Ladd NBs. I thought the cupsole would feel like too substantial a barrier between my feet and board, but after I got used to it I didn't really mind (tricks felt the same) and my feet felt better.
I switched back to vulc after I found some Blazer highs with lunarlon insoles. Best shoe I ever skated, and I used the lunarlon insoles for multiple pairs of shoes. Haven't been able to find Nikes or Cons with lunarlon insoles since. I've recently been skating Vans with Ultracush 3D insoles. I wore them with the Chima 2s they came with, then switched them over to some Style 112s and that combo works pretty well. Never tried aftermarket insoles though - still fantasizing about finding shoes with a lunarlon insole in 9.5...