On your actual question - what is the observable - I think the honest answer is that there isn't a clean one, and that is the most important thing to understand about this whole category.
Why you cannot see it
The old failure mode was deindexation, which is loud. You check the index, the sites are gone, you know. That still happens but it is now the rare case. The current failure mode is that the links from your network stop counting, and there is no signal for that anywhere. Your sites stay indexed. They keep their own rankings. Your money site simply does not rank as well as the link count says it should, and you have no baseline to compare against.
This is the reason the shared-IP debate never resolves. Both sides are describing an outcome that neither can observe.
The closest thing to a test
What I would do in your position, and I have done a version of this:
- Pick two of the six linking sites. Remove their links to the money site entirely, not nofollow them, remove them.
- Wait eight weeks past the next confirmed crawl of those pages.
- Measure the money site's rankings on the terms those pages' anchors targeted.
If nothing moves, those two links were already worth nothing, and you have learned something concrete about your network for the price of two links. If rankings drop, they were counting, and the whole footprint question is academic because it is currently working.
I have run this once, on a smaller network, and two of three links turned out to be doing nothing. That was more useful than any amount of arguing about IPs. It is also uncomfortable, which is why nobody does it.
On the config itself
Nothing in what you posted is a problem. Same nginx, same box, separate certs, separate registrars is well past the point of diminishing returns on infrastructure. Spend the effort on nullroute's outbound link pattern instead, which is the only item on his list that I would call urgent.