Spoiler Thread: Avengers Infinity War

Based in that quote. I find your admittedly interesting scenario a moot point. Thanos' statement assumes the other half of humanity will remember everything, he simply hopes Stark is one of the people they hold on to as a hero in their memories. Also, the fact that everyone left was in shock over seeing all their friends turn to dust says that isn't where they're going with this.

I take it differently. Thanos didn’t know who would turn to dust and who wouldn’t. I think his point is Stark was going to die either way, but he hopes he isn’t dusted so people will remember him.

I think Thanos fully understood what was going to happen, that these people would be wiped from existence. He respected Stark and hoped he wouldn’t be one of the people who would be.