Spoiler Thread: Avengers Infinity War

He used the Teserac(space stone) to get to Vormir, but couldn't get the soul stone from there and instead was relegated to being Charon of the Soul Stone. Iron Man did lose Spiderman, so maybe just suffering a great loss was enough to qualify him. In his mind, it was by his own hand as he gave him the suit and he died just like he said he would. This would also make sense in regards to the one path Strange saw, forcing Tony to be saved.
it's not a catch 22, but i can't think of what it would be called - as soon as you decide to kill someone you "love" to gain power then you don't really love them
i know if they played out that idea it would be a conundrum, but...