New Arm or New TT and arm?

I've been listening to a VPI HW19 11 turn table with the Eminent Technology 11 air bearing tone arm for the last thirty-two years, but I am now shopping for something new because I am fed up with piddling with the ET arm. Plan A is to put a new pivoted arm on the old VPI. Plan B is a new table and tone arm, possibly the Clearaudio Performance DC Wood with the Tracer arm. If anyone has any suggestions regarding the best pivoted arm to put on the VPI or comments re: the Clearaudio table or alternatives to it I would appreciate reading them.   
Doesn't appear to get mentioned much, but the VPI HW 40 DD at it's price point sure looks attractive.

No belts/speed to fuss with. As  VPI fan, I'd be all over that. Spend $5K on a future cart and be done.
I've been using the Origin Live Conqueror for about a dozen years now. Highly recommend Origin Live. One of the pitfalls of some arms is you wind up in the situation of being limited on cartridges, worrying about compliance, mass, etc. Read Mark Baker's philosophy, when the tone arm is correct these things fall to irrelevance. That has been my experience. You can buy and arm that is a lot of trouble if you want. Sounds like you maybe have had enough of that though. 

Next thing about Origin Live, the lead is integral. Arms that require an interconnect might seem like a good idea but it adds a lot of extra connections to a very delicate signal. Also then you need to spend and find a good phono interconnect. $$$ Another feature in favor of Origin Live. 

Mounting a new Conqueror on your VPI will be a major upgrade. Huge. Then if you are still happy with the VPI you could get another huge upgrade simply by putting it on something like a Townshend Platform. Or you could go to a new table. Even with a new table though the Townshend would still be a major upgrade. I put Pods under my table and it was a major improvement, and my table is on a 750lb rack of solid concrete, sand, and carbon fiber!  

The basic HW 19 table is a very well made, high performance platform.  If it has been maintained properly (meaning nothing more than not abused), it should be fine for use with any of the top tonearms out on the market.  I agree with millercarbon that it makes sense to buy a topnotch arm first, and then upgrade the table if you are not completely satisfied with that change.

Unfortunately, many of the better arms that could be had for reasonable money are no longer on the market, particularly after Jelco ceased operations (they were the OEM manufacturer for a number of brands, such as Ortofon).  Origin Live offers a variety of arms at a pretty wide range of prices, and their arms are decent.  At fairly dear prices, I like the Triplanar, Basis Vector, Kuzma 4-point, and SME V arms.  Other top contenders include the Shroeder LT and Reed tonearms.

I have heard a Clearaudio table with the Universal arm, but not the Tracer arm.  I liked this setup because I like poised, rich, and quiet sounding combinations (surface noise is well damped), but, others might find this sort of sound to be a little on the "dead" side (matter of taste).

Good luck on your search.
I lived with a HW19 jr through MKIV with an ET 2.5 for over 20 years. I experienced many noticeable positive sonics with tweeks on the tt. I ultimately realized the tt base was too resonant to overcome to provide the level of musical pleasure I wanted with these tweeks. I'd go with another tt/arm.

Wise move, Sell the whole shooting match. The Clearaudio is a good turntable for the money. I actually prefer the Thorens TD1600. It is suspended and isolated and has a very decent tonearm. It is also $1K less expensive so you can spend more on a cartridge:-)
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I currently favour the Music Hall mmf 9.3 or 11.3

They seem to have got almost everything right and you would be moving forward with newer technology

About the only thing they are missing is a one piece harness, which I like very much.

You could try sending Jeff at Audiomods and email to see if one of his arms would fit your existing TT. He sometimes makes mounting plates to make installation a breeze

I’ve had his Classic Series three arm with a one piece harness and micrometer VTA adjustment for about 6 years and love it.

Regards - Steve
Now is a great time to revisit direct drive imho. Of course Technics, but also Brinkmann and STST etc.