I am sure your transport is just fine to get started with a different dac...I wouldn't worry about this right now...pick the best dac you can...technology is changing fast...can likely pick up some that were "the best" just 1-3 years ago for less than 1/2 off list (or more)
I loved my Wilson's just a killer great speaker. The Rockports go in a little different direction...and are harder to drive...but they have their rewards to!