THE BEST $2000 TURNTABLE - NEW OR USED ??????

No such thing as "best". There are lots of good choices within your budget but a VPI sounds different from a Linn sounds different from a Basis sounds different from a Nottinghsm sounds different from a Rega and so it goes. We all have a bias as to what we like. I recommend VPI but there are lots of other good choices.

I agree with Narrod. It's what sounds best to your ears! I would suggest by my own liking, Michell ....

Comparing TTs is one of the more difficult exercises. There's no shortage of strong opinions on the subject, but I doubt many opinions are based on comparing TTs with all variables fixed (e.g. same arm, same cartridge, same phono stage, same platform, same system, plus careful TT set-up. A magazine reviewer's opinion might be more worth following, since at least a magazine has the resources for a proper comparison.

After tinkering with TTs, one of the few things I know for sure is that variations in platform & siting may be as significant to the sonic outcome as variations between TT designs.

A $800 phono stage to equal your $2 TT may be tough to find. Perhaps a used BAT or ARC PH-3SE or later model.

I understand that choosing one turntable over the other is a preference decision ( I can't argue with that statement since we all have different taste in music & sound. If this wasn't truth we will be listening to the same brand of speakers etc. ) but I would like you to guide me in the right direction. Maybe you can suggest different approach in finding the next best thing from what I have right now.

I don't know if it helps but I mostly listen to classic & vocal jazz, blues & pop. My system with exception of Cyber 222 MK II tube preamp is listed below ;

Vandersteen Quatro - speakers
Consolance Cyber 800 - tube mono blocks amplifiers
TacT 2.0 - preamplifier/room correction, modify
Rega Apollo - CD player
Music Hall MMF-7 turntable with Creek phonostage
Sonos wireless music system with Nixon tube DAC
Stax electrostatic headphones system
VIDEO
Krell Showcase surround sound processor/preamplifier
Optoma HD-80 1080p dlp projector
Westinghouse 47inch. LCD 1080p
HDDVD-Toshiba
HP Slim line media computer with 1080i card & 201 Sonny DVD changer accessible-operated by Media Center
Rel subwoofer - active only when watching video
various conditioning, voltage stabilizers, diffusers absorbers bass traps & tweaks.