FWIW... From my experience, most definitely, a DAC will improve your MP3 playback. It should get rid of lots of harshness. I'd get a glass toslink cable and connect it out of your computer.
If you're using a Mac then it's even easier. Set AudioMidi to 25/96 and you're good to go. Mac's however, outputs through "mini-toslink". You can get a Vandenhul Optocoupler II for $100 (as good as it gets for optical cables get from my understanding) with a mini on one end and a regular toslink jack on other end. Or if you need a longer one, Parts Express has a 12ft glass one for $65.
Or, if it's MP3s anyways, you can simply get an Airport Express and stream your music. It has a DAC in it, and from my experience with a NAD 325bee, it sounded noticeable better through the AEx then a Y-cable straight from computer or ipod. It's $50-90 (look on Craigslist) and you can always return it...
This is your cheapest route.
For $300-350 used you can probably get something very nice these days. I'd go with a tubed DAC if I were you, so you could tube roll later (change sound for cheap) and "color" the MP3 sound. I'd probably look for these ones, as you could re-sell them easily if you don't like it:
-MDHT Paradisea+ (older version)
-Channel Islands vDAC (or something like that)
Hear lots about this one on another forum, but never tried it:
-VALAB Dac (sold on ebay for $200 new).
-the DAC Magic mentioned also gets a lot of mention in other forums as well. No experience.
I really like my Monarchy M24, it's a tubed DAC with a separate tubed linestage/preamp (2 power supplies), but it's $700-800.
I've been very curious about the Paradisea and Valab though.
You might want to lurk around this forum:
http://www.computeraudiophile.com/content/Help-DACs-please
People on Audiogon seem to think MP3s are an abomination.
Also try to get 320 kbps files at least... try mininova.
And I don't think there is any point in converting MP3 files into large "CD Quality"-full bit-rate files, other than wasting storage space. As far as I know, once the bits are compressed and gone, there is no way to restore them.
Good luck. Send me a PM if you have any questions.