What's my best upgrade options

@dothebluecolts 

The best upgrade would be a new defensive coordinator.  The run defense lost the last game.  Second, can we remember Andrew Luck?  The same ending will likely happen with Richardson if he continues to run the ball. 

Whoops!  Sorry, we're talking about audio.  I agree that the TT is the weakest link.  I'm surprised no one has mentioned an updated dac, or maybe a transport and dac for playing cd's.  Streaming?  With those fabulous speakers, the sky is the limit.

Go Colts!

Absolutely your front end. I would give carefull consideration to the future of your system. The future is streaming the past is vinyl and CD. Concentration of your money into one approach will get you the farthest most quickly.

The strengths of your system is your speakers and amp… and maybe the preamp.

So with that in mind, you could set yourself up for future upgrades by getting a really good DAC. Something in the $5 - $10K new… used, bringing the cost down. Then use your CD player as a transport. Then as soon as you are able to recover a really good streamer (Aurrender) Then you are set for the future and you’ll have a 10 million+ album collection for $14.99 / month (Qobuz).

Is vinyl your primary source? Will it remain your primary source?  If so, the consensus suggestion here is correct in my opinion.  Your turntable rig needs a meaningful upgrade that is not a Rega product, especially if you have a ton of records that you (like me) are actually going to play. Spend the money now, and take comfort in knowing that great turntable/arm combinations will outlast us both.
 

Good luck 👍 

The OP didn't mention streaming, but that was my first thought. 

Before I bought my Innuos Zen Mk3 streamer, I used my Denon DCD-1700NE sacd player more than anything.  I tried the vinyl route. Spent around $4500 on a TT, Hana cartridge, and Sutherland phono stage. It sounds great, but I'm not into the cleaning and flipping of records.

I run the Innuos into a Gustard U18 ddc then to my Gustard R26 dac. Also using a LHY ock-2 clock and decent cables. This combination sounds better than the sacd player. 

gonna have to agree with many other posters.  a $2k turntable with $25k speakers and $20k amp/pre (when new) is out of balance.  you could probably get a pretty nice TT for $5k, but I wouldn’t bother if you’re only willing to spend $2k; I’d just plow that into a better DAC and call it a day.