the way i see it, a lot of this gear madness stuff has to do with the fact that a wide variety of gear can work for you. i've skated fine on everything from an 8.125 on forged hollow trucks, to a 10 inch shaped deck on standard trucks. its really only been on some extreme setups that i was like "yeah i cant do this".
buy an 8.5, skate it til it dies, see how you feel. i think the real key is your skateboard should feel like home.
for what its worth, the best setup change for me was going to an 8.5 and conical wheels years ago. all the tweaks i made since then didn't help me improve much. you'll notice if it's better or just different.