I did an installation kind of like what you are describing, but the construction of my house may have allowed for a less destructive installation. The house is wood frame, raised foundation. My equipment cabinet is against an outside wall. My speakers are on either side of a fireplace. I ran my speaker cabling into the outside wall, down through the sill plate, under the house in the crawl space, back up through the sill plate in the same wall, and then through the wall. Each time, only a small 3"X3" hole was required...small enough to be covered with a wall plate through which I ran the speaker cable without an additional connection at the wall. The wall plates were standard cable jack plates with the cable jack removed and the remaining hole enlarged with a Dremel tool.
I should mention that the same method was used on an inside wall for the other speaker. The installation was part of a larger project, and the whole thing was done by two outstanding local home theater installers for about $350. Well worth the money for the clean installation.
Other cables, like power cords, are hidden behind floor length drapes. A power conditioner and power supply for my VAC amp are hidden behind a chair. Fairly clean looking.