2) There is also another story where he talks about dropping out of high school to support his mom, and being a shoe shine boy. I'm pretty sure it is not related to #1 because this one is a conversation between him, Tony and Pepper, not the whole team.
I don't recall if they were gen or shippy, but I honestly don't care either way. I just want to read more about Steve's personal experience of the Great Depression. Recs also wildly appreciated--you have my undying gratitude. =)
ETA: fics found, but your recs would be lovely.