Always source first you can’t reproduce what isn’t there to start with. 
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Where does the second PS go?
ND555 looks to be about £18k new or £11k s/h but fairly new.
500DR looks to cost £27k (!) new or £11k s/h - non-DR units seem to be available for little over half that.
Getting either at £8k from a reputable seller looks a great deal.
I have B&W 804 D3s, so a bit smaller and less demanding than yours. They really benefited from going from 250 to 300DR. I can easily imagine that the same would happen jumping from 300DR to 500DR with your speakers. However, I have never compared ND555 to NDX2 with PS, and expect that I would want to hear both options before spending this sort of money - unless I knew I was actually going to buy both and have done with upgrades. For the foreseeable future.
Good luck!
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8k for each is a very rare opportunity.
Got my 552 for a steal (8k €).
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500DR would be my move. I went 500DR first, then upgraded LP12 which is my main source and 552DR at the same time.
I have NDS with 555PS. Am leaving this 2nd source as it is for a while.
You won’t be disppointed with the 500DR. It is an absolute beast of an amp.
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Your speakers will love the extra power!
Going from ndx2/555drps to nd555 was a large improvement in all aspects of the musical message
I thought that adding a second ps was almost as large an improvement.
If budget allows you won’t regret the second ps.
Hifi plus did a review of nd555 with 1 vs 2 power supplies
Google this it’s a nice read. It will explain the difference better than I can.
David
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The second ps is already in the Fraim - but I want not to do all in o e step 
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Get it powered up man! What are you waiting for?
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mate do you have two 555 and your only using one? your fiddling is weak today!haha
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Yes, I bought both 2nd ps and 500dr together and I promised myself to install it stepwise. And so I did!
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Wow that’s special forces level of discipline. You are like the hifi ninja.
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I had NDX2/555PS with my 552DR/300DR and moved to a ND555. As good as the NDX2 setup was, the ND555 is a other league all together, and that would be my recommendation. A 500 would only amplify the limitations of the NDX2. Source first is the obvious route here.
It is More a way of getting rid of doubts. The 500 Must First fully arrive in my ear. If so - Next one.
I have Already done 2x SL together with 500
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Wowzer what a review. ND555 is a must try and the second power supply an ambition clearly
Nd555 was my entry drug into 500… 1 year later… full 500… 
Nd555 is wonderful
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Yeah I am taken. Honestly it’s all a bit of an accident. Adding speakers first meant I knew I wasn’t getting the best from them… but putting in the 555ps and a 552dr just blew me away. My enjoyment of music is reformed to a new place.
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You can do it I do now…
Buy both 500 and nd555 and put them in stepwise 
Thought a lot about adding the second ps (which is already fraimed).
But as the 500dr (together with 552) is so different, I really like to adapt first … and 500dr is not even warmed up properly…
I have done way to fast upgrading as offers came up (you might know) and coming from olive it is an adaptation journey …
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Have you tested whether it works?
I agree with HiFi + re the additional PS for ND555
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