Upgrade entry level or start over?

Good variety of worthwhile upgrade suggestions.  Any one of them would result in sound quality improvement. I believe that a better quality phono stage is a very good move. As I think it is the "weakest link" bottleneck item in this audio system. 
Good luck, 
Charles 

This is the very reason why I find vinyl so frustrating, it takes considerable money to make a noticeable impact. I've read in many phono stage reviews that it's nearly impossible to find a fully capable phono amp for less than $2,700.00. I'm not so certain whether or not this is true but will say that in relative terms, investing $3,00.00 in a phono amp. cartridge and turntable would be considered 'budget entry level'.

I agree with those others who believe that your focus should be on a better phono amp. I believe the chain towards improvements goes; phono amp, cartridge, tone arm, turntable but this could be an over simplification. The question is whether or not you'll really notice a difference between your current phono amp and the one you'll be able purchase for a $1,000.00?

So if you go the phono amp route, then I'd say try buying one that's used with a rating of 8/10 or above. My phono amp is an ASR Mini Basis Exclusive and is a really good phono amp for its price range. I've seen older used models of the ASR sell for about $1,500.00. 

@goofyfoot

Yes, I think it is most difficult getting into high end audio and vinyl... this is where it is most hazardous... of making some investments that do not get you what you are hoping for. I have to admit that once you get above $3K for a Phono-stage the going gets easier. But you can also put a better sounding analog end together for $3K total 10mm than digital (assuming you choose wisely... the hard part). But then a digital end is a streamer, DAC, preamp, and amp... that’s quite a string.

I think all of us who have stuck with this have had a seminal moment when we made a choice that completely blew us away... exceeded out 10mm wildest dream. Mine was I bought my first piece of true high end electronics... A Nakamichi Dragon tape deck.... it was so much better than anything I had ever heard... not by a little, by more than I though remotely possible.

ghdprentice, I just believe vinyl to be the least cost friendly. A great phono stage is a minimum $2,500.00. An excellent cartridge is a minimum $1,500.00. A solid tonearm would start about $1,300.00. A dependable turntable like a Rega would start at around $800.00. Now were already at around $6,000.00. Think about what could be done with $6,000.00 where it pertains to digital.

@goofyfoot,
Agree with your example, reasoning and math. I’ve heard many examples of both  very good sounding analogue and digital based systems (I'm not into the tiresome analogue versus digital  battles).  Analogue IMO has a higher cost point of entry. Buying used certainly helps (When feasible) but same would apply for finding higher end used digital as well.

6K dollars could definitely buy a genuinely excellent sound quality digital front end as you note. No doubt the OP can improve his current analogue performance. It will require patience, additional research and prudent purchases.
Charles