You'd be better off getting new pre-drilled bars. The first set I did I just drilled out the dimples. I couldn't get the holes as smooth as a machine can, which could eventually cut wires. Plus since I only drilled the dimples you could still see the wires and it looked kinda cheesy. I think the ones I ended up getting was Cycle Smith. If you decide to drill new holes where they will be hidden, you'll still have the dimple holes exposed.
You at HUrlburt PJ training? I was there 90-93, 8 SOS.
Definitely get new bars. The best way to reroute the wiring harness is to pull the dash and remove the wires from the connectors using a pin extractor and reroute your wires thru the bars. Then reconnect the pins in the proper holes in the connector.
If you need extra lenght for your wires, you can spice the wires under the dash and re-solder for a cleaner installation. Use heat shink tubing after you solder to keep the wires from being exposed and cover with another "sheath" if you have one.