Can I match or beat my digital, and at what cost?

Hi folks,

I had a friend bring over an old Kenwood TT ( KD1033 ) and a phone preamp, JEC it looks like. Well it sounds pretty good and has me interested in trying a vinyl setup now.
The frequency extremes and the layering aren't there that I am used to.

Say for 1k total budget..how close can I get to my current digital? I will likely buy new from my local dealer. They have Rega so I was thinking of starting with a p1.

Current system is
Audio Reserach REF2 MK2
Proceed HPA 2
Musical Fidelity A308 CR
Martin Logan Ascent
all transparent Ultra MM IC and Speaker cable.

Thanks for any advice.