Derangedteddy

I also find it best to do my mixing with a set of quality headphones. I have a pair of Bose tri-port ($120) headphones and they're great for mixing. You could also get away with a pair of Skullcandy TiTANs ($50) if you like earbuds. I also use these somtimes. Although their mids and highs aren't quite as clear, theyr'e wonderful for bass.

The problem isn't necessarily going to be the music itself. The speakers are going to be your main barrier. All that a subwoofer does is take frequencies below a given value (usually around 100-120Hz and lower) and amplifies them. If you mess with the arrangement of the song, you may have problems with people on other speaker sets lacking bass. You should get a DSP in your media player that can handle frequency cut-offs and gains to make it sound like it should. I personally use Winamp with Jammix enhancer because it allows full control over hi-pass and low-pass filters, etc. And there are several profiles that you can make. I have one set for my home theatre, one for my car (so I don't blow my speakers lol), and one for my headphones.