Well that depends on how high you are going to go with an overclock.
On a stock cooler, i would be skeptical to push it passed 4.0 GHz.
You can get a closed loop water cooler, pre-assembled for about $50, and that should serve you well.
Should be able to push the MOBO and CPU combo to it's limits.
One thing i am noticing, looking at your list here, your MOBO is a micro ATX, and your tower is a Mid Tower ATX.
Will have a compatbility issue there.