My FAVORITE way to get around Charleston streets, which are notoriously shitty is this:
Any 8.5 or larger board
1/4" risers
Powell All Terrain Formula Wheels-like 56mm or something a little bigger maybe
Whatever trucks you can find that'll fit--I got trackers and they're fine
I am still going to get a little zip zinger or a similar shape for fun, but if you really want to get around a city, having a normal shaped board is awesome because you can ollie up curbs and over sewers or whatever. In my opinion, they're just a lot more fun to ride.
I'm still experimenting with wheels. I really like the ones above because they are soft enough to get over bumps, but not too soft to ollie on. Recently though, the "core" or whatever broke on one of the wheels and it's a real bitch to get the bearings out.
What wheels have you guys had good experiences with for cruise boards?