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.