Ok, since you were a self-proclaimed noob, I just thought I'd ask.
Some more possibilities might be to consider including fields such as the analysis info: BPM, Replay Gain, Album Gain, Intensity, Peak Level.
Stacking of files might also be a possibility - I haven't tested out how this would work in practice. You'd stack duplicates, and include only the Stack Top or non-stacked items in your smartlist.
The bottom line is that MC works on a file-by-file basis, so has no concept of the type of grouping you're asking for. Hopefully any of these tips will help you find a workaround.