Thanks for the detailed answer. I think I'll keep these speakers for now as they are fine for the price and continue to do research. How to include a subwoofer to the system? Using optical connection? The speakers don't have any out put connection for subwoofer. M-audio speakers definitely lag in bass.
In the case of your m-audios, the least bad option to add a subwoofer would be to get an active sub (most of them are this days), with stereo input, and use a stereo Y splitter out of your mac into both maudio and sub, with a little loss in signal and probably quiality too, and the big downside that you have to level the volume of both sub and speakers manually and then use your volume control in the mac as main volume.
If you want to add a sub, please get a quality one, not too big (8" is more than enough), with adjustable level. You want quality and not quantity when it comes to low frequencies, the sound must be tight and controlled, not wobly and out of proportion... when a sub is best set up, you should not be able to tell the thing is there. HSU, Paradigm and many others have great small subs for good prices.
You mentioned 'keep attenuation in the analog domain'. Does it mean keeping the volume knob on speakers at lower setting? Also, please let me know about the software add ons for itunes to make the sound better.
Regarding the volume, what I would do is set the mac to max, then set the maudio to a low volume (so you don't hurt your ears) and start adjusting in the maudios until you find the level you want. If you get some distortion in a low volume in the maudio, lower the mac to 90% and try again.
Software wise I can't tell you much, as I don't use itunes at all, but I do know that "Amarra" is the prefered plugin and some consider it a must have, it'll cost some money... $99 for the junior version and up from there.
I like to use XBMC, it's open source and the sound quality is not bad at all, plus it plays whatever I throw at it, music and videos.
Now, if you're serious about getting good music quality, the question "how much do you want to spend?" comes in order, for example a peachtree audio iDecco or iNova, together with wharfadales diamond 10.1 or 10.2 speakers, or paradigm atom monitors, plus maybe a good subwoofer will get you top quality sound for your desktop, or in the headphone world a burson audio HA-160D paired with senheinser hd-600 or akg 701 headphones will do great too. But all this options will be as much as for a new body or a fast zoom from nikon or canon, and it can only get worst from here, but is well worth it.