How much do I need to spend to make vinyl sound better than digital?

All,

I have a solid vinyl setup that I like to think of as entry-level “plus:” Project Debut Pro with Sumiko Moonstone cartridge.  I enjoy vinyl for the ritual but find that my digital gear - a $400 ifi streamer and the AKM DAC built into my Anthem preamp - beats the analog rig in most ways.  Far better imaging/soundstage and much tighter bass without the occasional distortion/sibilance/warbling of the vinyl rig.  I haven’t messed with cartridge setup other than to check the factory-performed alignment, which looks perfect.  The table is perfectly balanced, counterweight set correctly with an electronic scale, etc - so I have no reason to think there’s a setup problem.  
 

Is this par for the course for this level of vinyl gear?  What do I need to spend to get my vinyl gear to match the performance of decent digital?  I’m thinking of upgrading to a Clearaudio Concept, perhaps with a Hana SL cartridge, but I want to make sure doing that is going to deliver a fundamentally different experience than what I have right now with the Project/Sumiko combination.

No interest in flame wars or rehashing the vinyl/digital debate.  I know vinyl can sound wonderful and am simply trying to decide whether I can afford the price of entry for a system that can gets the basics right (no audible distortion/sibilance, decent imaging).  I thought the Project/Sumiko would have gotten me there, but for whatever reason it hasn’t fit the bill.Thanks for any insights.