the object of that image is practically (and I think theoretically?) timeless.
Indeed. I’m just a guy who took college physics and then watched a lot of YouTube videos. But from what I have gathered, things that fall in almost completely freeze in time as they fall. So if an outside observer were able to see them (they won’t) it would look like more and more stuff getting stuck on a slowly expanding shell around the singularity.
What I find interesting is that over insane stretches of time, Hawking radiation evaporates the hole. So if you were able to survive it (you won’t), falling in would look like the universe suddenly speeding up, all stars die, and before you even reach the singularity the black hole evaporates and explodes. Leaving you in a dark, cold vacuum.
At which point the big bang possibly happens again, but that’s another story.