thanwu,

My house has trim/molding at the bottom of the sheetrock. As mdrew suggests it was easily pulled off to run the wires. Then up to surround height with the tool from Home Depot.

If your house has trim I think it's not too difficult for a beginner, I am not handy myself. Through the attic sounds difficult.

Home Depot also had speaker wire feed throughs which look like an AC socket plate.