It just so happened after installing Vocaloid 5.0 my hard drive crashed and Vocaloid 5.4 was announced. And, after the Time Machine restore it would not update on my Mac from the DMG According to the Vocaloid Website, if you use Apple Time Machine and Vocaloid, it is beyond the scope of their Support.

https://www.vocaloid.com/en/support/download/update_v5e/

I found that by reinstalling the original 5 over the previous install, I was able to reinstate the path well enough that the 5.4 Upgrade did install from the DMG. Hope this helps others in a similar situation.