I guess it would depend on where I felt I have the most to gain based on what's available on the market. If you're in love with your speakers and never heard anything in your budget that makes a material improvement then I'd apply my funds to the table....and vice versa. But....there are lots of $12K-$15K speakers that I feel sound as good as speakers twice their price but there are very few $10K tables that sound better than the best $20K-$25K tables. If you're really pleased with your speakers I think you'll reap more rewards on the table (and cart!)....that's just my perspective.
What to upgrade to?
I will be retiring at the end of the year or earlier depending on the Covid virus. Anyway I am looking for that last upgrade to my system. I will be looking at either upgrading my analog system or loudspeaker. I have about 10k in a complete turntable and my speakers retailed for 12k about 5 years. Both I could live with in retirement and be quite happy. But I have $15k - $20k to spend if I want to on either upgrading my turntable or speakers. What would you upgrade? Turntable or speakers?