Trouble with -set smoot-

So, I am working on my first big project: A motorcycle

I started by making the back wheel.

So when it was ready i wanted to get rid of the blocky effect so i tried -set smoot-
but as you can see on the break it gives this crappy effect.

I tried flip normals in edit mode but it didn"t work.

Does someone knows a trick to make it smoot and good looking?

(P.S. subsurf makes it even worse)

Greetings, Bullseye

Recalculate your normals (CTRL-N). If you’ve modelled the wheel correctly this should fix your problem.

go into edit mode, press w, then go to remove doubles that im almost sure is the problem

Well removed doubles and deleted about 36 verticles

and flip normals doesn’t work

it looks better now but still not good

btw i did a boolean operation on the break to get holes in it so in edit mode the mesh is totally screwed with verticles

this might be the problem?