I think this is a good point. She seems pretty interested in living a high life, and not so much in from whence the funds for that.

Though I wonder what it means that Pepper wasn't dating Tony until he was a superhero. She was his Girl Friday for ten years or so before, but they didn't start dating until IM1. After which they were on again/off again.

Though of course she still cared about him before, and the dating could have started for I Thought You Were Dead related reasons.