to the OP.
i think that your analog rig is below par as compared to your digital front end. I was in the same boat as you a few years ago and now, i beleive that my analog is on par with my digital. Just one advise first... your source vinyl plays an important role. it has to be a very good cut.
i woulld look at the Rega P3 tables or Technics Sl1200 series,
then if you like a get up and go cartridge, then look at the Dynavector line or if you like a smooth but transparent cartridege, then Hana is what i would research into
as for the Phono preamp. look into Parasound Jc Jr model. .
your preamp has a very good DAC and streaming technology is very very good nowadays.I guess under 5K should get your analog gear on par with your Digital