So, I ended up going with DT990 pros, fiio E9, and a xonar DX 7.1 . Thanks to some ebay best offers and ~$30 of amazon credit, I managed to get everything for under $300 new so, definitely "mission accomplished" for me price-wise. I'll update one last time with my impressions once everything gets in if anyone is interested.
I'm in the same delima as you. Are you happy that you went with the DT990 pro's? What Ohm setting did you go with and whats the difference between all of them?