Personally speaking, I noticed a bigger upgrade with my DAC than amp for my SR-225i. The DAC drastically cleaned up the sound, while the amp helped bring out the sound better (better soundstage, silent parts sounded much more black, much better instrument and vocal separation). I don't think the amp would have been nearly as effective without a much cleaner source.
For $300, I'd recommend looking into either the pico DAC (http://www.headamp.com/pico/pico_usb_dac/index.htm) or ask MisterX if he can build a AMB gamma2 for you (near the bottom of http://www.amb.org/audio/gamma2/). I think you can get a significant upgrade in your sound with a $300-400 DAC and a similarly priced amp down the line (such as the Schiit Asgard or Lyr). They hold their resale value pretty well, will last for a long time, and are well regarded in their price bracket.
There are hundreds of pages of discussions on the pico and gamma2 on head-fi, and reviews all over the net:
(I'm not sure if linking to other review sites is allowed. just google: headamp pico gamma2)
http://www.head-fi.org/forum/thread/466453/gamma-2-vs-pico
http://www.head-fi.org/forum/thread/430793/gamma-2-2-dac-thread
Another option to consider is the Headamp USB DAC/amp: http://www.headamp.com/pico/pico_dac_amp/index.htm
http://www.head-fi.org/forum/thread/420713/review-headamp-pico-usb-dac-amp
Edited by Elysian - 8/14/11 at 2:35pm