Does anyone else feel unnerved at the growing subconscious recognition of some kind of dark age ahead being possible?

It's completely ordinary for there to be substantial loss of culture due to tax wheezes, insolvencies, reorganizations, hacks, mistakes, lack of forethought.  Nobody has been disturbed enough by what's happened so far to do much in the way of organised efforts that will make a difference.  The internet archive is great, but it's centralised.

If you look at the vulnerability of Western power grids, the dependence of tech company budgets on advertising revenue, the leverage of even boring companies like IBM as we go into an extended financial, economic and then sovereign crisis that's going to be intense, then it's not crazy to be wondering about dark ages for the West, or at least information and cultural transmission loss events of critical importance.  Tbh as @JucheRespecter observes, mimesis has already failed in transmitting cultural knowledge.  That would be partly possible to reverse but people don't want it enough.

The monks preserving Western civilization this time around might include the data hoarders.. it's going to be a slightly... incomplete and unbalanced record that survives.