How much play is too much? And should I pull my console looking for a broken bushing? Or does this look normal for a ‘99 with 192k miles?

 

Interesting. I've never had an automatic, and didn't realize they have the same issue. I think the official advice for manual transmissions is that when it starts jumping out of gear, it's time! But of course a lot people, myself included, have replaced the bushing just because we wanted to tighten things up. And it makes a huge difference. Sometimes you open it up and the bushing is in pieces.

 

I'd pull that apart. I don't have an auto 4Runner (2 5-spds in the household) but I've pulled them apart in the PnP yards before. There's a fairly substantial pin holding that lever, and some plastic bushings. It's likely that the pin has come loose and out of one side, and it's only going to get worse until you put it back in place.

Or the bushings are shot:

 

The 4 blue bushing failed on my 98 at about that same mileage. They seemed to degrade quickly and I think I had even more play. Go for the 4pak for around $10.