It really depends on what one considers as a "starter system;" at really low prices, digital players are vastly superior to cheap vinyl rigs which not only sound terrible, but also risk damaging records. But, improvements as one moves up the price/quality curve for digital gear is less dramatic than is the case with phono gear. The OP is placed quite far from "starter" with both setups.
I would recommend that the OP first look into loading issues, and perhaps VTA--both are common sources of problems with shut in top end. Excessive loading (too LOW a value for the resistance) and too low VTA, can cause this sort of problems.
Once performance is optimize, it might well be the case that the OP still favors the digital rig, probably because that sound is more familiar to the OP. It may take some time, but, with setup optimized, the virtues of the vinyl sound may become more evident. This is sort of a learning process and familiarity is important.
I personally think both digital and vinyl setups can deliver great performance and I will not take sides in any sort of religious war. I think there are far bigger differences when making other sort of audio choices: high power vs. low power amps, solid state vs. tube, electrostatic vs. dynamic drivers, planar vs. point source, and so on.
