Analog vs. CDP: A fair comparison?

Ok, in summary, I'm planning on selling my Cary 303/300 and taking the funds and buying a TT rig including Table, Arm & Cartridge. I'll worry about the phono stage, record cleaning machine, etc. later.

Assuming I get $2,500 from the CDP, will I be able to get a used rig that will at least match the sound quality? Assume also that I will have a phono stage budget of $1,000.

Rest of the system if Cary 300SEI.

Is this a fair comparison? Or, will the sound just be different (i.e. tubes vs ss).

thanx much