What's my best upgrade options

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.

You didn't mention your room.  Every flat surface in your room is a transducer that reflects, cancels and muddies the sound.  How much does you sound change when you stand up?  How about when you lean forward in your listening chair?  Unless you have already treated your room I would suggest purchasing a couple of acoustic panels and just lean them up against wall and then move them and listen.

A simple heavy blanket over your flat screen increases clarity and depth.  If you have a coffee table between you and the speakers try moving and giving it a listen.  Acoustics don't have to be permanent but simple changes can make a difference and then can be removed for returning the space back to a more normal configuration.  You'll also learn what make a difference and when you want to make the changes for good you'll understand it better.