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
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.
It may be subtle, but if starts sounding different, have it looked at. 

I was typing on my phone, so my answers were kind of short.  The long version of the story about the diamond falling off was that I bought the MC-Two Special second hand.  When I mounted it and set it up, it sounded horrible.  That's when I took a close look and saw there was no diamond on the cantilever.  I notified the seller and they refunded my money and said they didn't want the cartridge returned.  That's when I decided to look into having it rebuilt.  At the time the person representing Van Den Hul was someone on Florida.  I contacted him and found out the rebuild was the same cost as what I paid for the cart., so I figured why not.  It took a bit (ok, a lot) longer than I was told it would, but was worth it at the end of the day.  I think you'll have a better and more professional experience with VPI than I did.  I wonder if A.J. is still doing the rebuilds.  I believe he's in his 80's.
Let’s not keep hyping the great vintage tables and cartridges so much. It just pushes the prices higher for us. Best to just not argue with people so much and let them buy their cheap belt drives and let them find their path to better sound on their own.