should i have a long USB or analog cable run?

I see you have a TT with a RCA/USB out, with internal preamp.

It's not a good idea to run a long length of RCA cable from a TT. First of all, it's analogue and unbalanced and can add noise or pickup RF. You would also need to know the capacitance of the cable in such a long run for best results.
Use the USB output.

Question...are you planning on reclocking your USB signal between the laptop and your components input?

Right you are Al. Once the ripping is completed, I was wondering if the OP intends to playback from the laptop to an external DAC in conjunction with his NAD.
IOW, what is the final destination?