I have owned every version of the Well Tempered table over the years from the very first ones produced. These are exceptional tables and I would not be in too big of a hurry to upgrade. The arm damping does make a difference, but easy adjustments will only be achieved with the Reference arm. I had the Reference plinth before the Reference arm was available. A later upgrade to the Reference arm was a stunning improvement particularily in the bottom octaves. With the budget you've allowed you could easily pick up a used Reference table and arm or you could just put a Reference arm on your Classic. Personally, if you've got the bucks and are really into vinyl I'd go for the Reference table and arm. That table is a thing of beauty. The VPI and Clearaudio will not necessarily be an improvement, just different. One additional thing I would mention is to consider trying the Grado Reference cartridge. I switched from a Van den Hul Grasshopper to this cartridge (mine is the original low output version at 1mV) on the recommendation of Carl Smith at Transparent and another friend with the same table. The difference was notable in my system and an improvement over the much more expensive Grasshopper in my system. This is a perfect match for the Well Tempered arm and extremely musical. Synergistic. The folks at Transparent have tried every kind of cartridge regardless of cost on this table and this is the one they recommend. Hope this helps. My system is as follows:
Well Tempered Reference w/Grado Reference (1mV)
Audio Research PH3 Phono Preamp
Pass Labs Aleph P (remote version) Preamp
Bryston 4B-SST (amazing amp that replaced a pair of BEL 1001 MK3A's)
Aerial 10T Loudspeakers
Cardas Golden Hexlink 5C Speaker Cables
Image Reference Interconnects
Dodson DA-217 Mk2 DAC
CEC TL-2 Transport
API Power Wedge 116 Power Line Conditioner
Set of 3 Argent Room Lenses
Well Tempered Reference w/Grado Reference (1mV)
Audio Research PH3 Phono Preamp
Pass Labs Aleph P (remote version) Preamp
Bryston 4B-SST (amazing amp that replaced a pair of BEL 1001 MK3A's)
Aerial 10T Loudspeakers
Cardas Golden Hexlink 5C Speaker Cables
Image Reference Interconnects
Dodson DA-217 Mk2 DAC
CEC TL-2 Transport
API Power Wedge 116 Power Line Conditioner
Set of 3 Argent Room Lenses