Which CDP exactly do you have. Even if it's old school, some old CDP have incredible DACs in them and you would waste your money buying a new DAC in the <$1000 range. If your CDP is old AND cheap/low quality, then using it as a transport into a good DAC will also be a waste of money because even though the DAC might improve a bit, the transport is as important as the DAC in my opinion, garbage in the DAC will only produce garbage out of the DAC. Obviously your cans are top notch so there is probably not much to change there for under $1000. If you have to buy a transport and DAC for under $1000 I would personally buy a Squeezebox and combine it with one of the "flavor of the month DAC" like the Paradisea, Citypulse, Zaolu, Dac-ah, etc... Don't forget also that good cables interconnect can make a relatively significant difference if you currently use el-cheapo ones... Have fun, I can see many headaches and hair pulling in your future when you start looking into transport, DACs, IC,... cheers.