Buying a new TT today


So I’m pretty hellbent on buying a new TT today! Or should I be?!?!? 
I started off kind of sour on vinyl several years back when I ignorantly bought a cheap TT that had a built in phono stage.... Talk about a disappointment! And a buzz kill for vinyl!
Anyway a year or so later I bought a Project Carbon Debut and it blew my mind!!!!  The step up in most aspects of the TT, carbon fiber tone arm/heavier plinth/much heavier platter/motor and remote position/better cartridge in a Ortofon m2red, along with the fact the it was now running through my Integrated’s Phono Stage was just such a leap in sound that I never expected, that now I’m looking for yet another leap like that again lol
Anyway, with pocket flush with cash and headed to two hi-fi shops I pause....
In my new price range, $2,000 or so, should I be looking for a new TT? Or a new cartridge for the TT I have ?
thoughts.
264win
Thanks. I live within an hour of VPI, so I would drive up there and let them handle it (and hope they don’t sabotage my Rega when removing or reinstalling the cartridge 🙂). Hopefully they can insure AJ dies it himself or maybe swap a remanufactured one for mine for the same cost.

Any idea how to know when it’s time?
So it either breaks or not.....just like a Rolex needs service when it stops working?

The sound quality doesn’t gradually get worse?
Yes, there should be signs - distortion, sibilance... you can have it inspected under a microscope for signs of wear.
Thanks and for the $25 word I just learned. Good to know it will be obvious.