Yeah, the toolbar Fredo has come up with is amazing. Makes me wish all the coders would collaborate and jointly work on perfecting some of the "must have" tools. Could you imagine how good sculpt tools, shape bender or some of the others would be if it incorporated Fredo's toolbar?
As far as a shape tiler ruby goes, I guess the most challenging part of that coding would be fitting the tiled shapes into a defined space and having the edges cut off accurately. It's interesting how LWCAD does it. If you see this video - http://www.wtools3d.com/swf/online_help/LWCAD_30/detailed_sidewalks/detailed_sidewalks.htm It's amazing how you can turn the array of tiled shapes as if it were a texture and have it still fit within the face.
I think a ruby like this would have to start maybe as a hatch tool of some kind, and then have the script fill every face in the hatch with the chosen shape. How would you guys perceive a tool like this functioning?