What really makes a story feel dated is not so much in the details you describe as in the themes you develop.
The "deep nod" is not a raspberry. It's acknowledgement that in those particular books I was reading, there's a little time capsule.Hurrah for modern stories that speak to our current times, and a deep nod to the old ones which let us see how we used to live and think.
I think there are quite a few great and modern authors, each generation has at least a few that stand out as the "voice for that generation".
But when it comes to "the greats," I think many look to those who have stood the test of time.
Personally speaking, most of the literature that I get really excited about wasn't written until at least the 50s.
So, an older book is a time travel device.