Only start with the wire upgrade if your pretty much done with component upgrade. I would start with IC on preamp to amp first along with power cords and do some listening then take power cord out and compare, then the IC and compare, you may find power cords make more of a difference and the same goes for IC, this will help you find the strengths and weakness of your preamp and amp, next I would do the same for CD/Transport and DAC again if you can try both IC and power cords this will help you best. last I would try speaker wire.
I find having good power cords helps in the what is better department when it come to IC. This is just my way of doing things and what works for me may not work for you! Happy wire hunting!