Without the benefits of having heard any of your components, a do know from personal experience that upgrading your DAC is one of the best bang for the buck moves you can make, so you would probably get a big boost out of a new $1,000 DAC.
Another suggestion is power conditioning. My best spend $1200 in audio in 2010 was a ps audio powerplant premier. These units will be hitting the used market in high volumes now that PS audio has released the new P5 model. You should be able to pick one up for $1,000.