Hi! Thanks in advance for putting time into this. I’d love some recs where Steve’s previous poverty/poor health are discussed or explored. I feel like those two aspects of his character are sometimes overlooked. Thanks so much!

Those are definitely often overlooked, and I, too, love fics that deal with them.  A lot of those fics are pre-serum or de-serumed Steve fics, to be honest.  I’m not sure if that’s what you want. There is a De-Serumed Steve rec list and a Tony Loves Skinny Steve list already.  A lot of the ones with Steve being poor are AUs.  Here are a few that you might enjoy along those lines, though:

EVEN WHEN YOU HAVE NOTHING, YOU CAN STILL LEAVE COMMENTS AND KUDOS FOR YOUR AUTHORS

i would shower you with roses if only they didn’t make you need an epi-pen by theappleppielifestyle:Tony has a plan to woo Steve, and is determined not to let Steve’s health issues get in the way.Which
is hard, because giving him flowers make him have a sneezing fit, they
have be careful about food because it seems like Steve is allergic to
everything, and they end up spending most of their dates in the hospital
after something goes wrong.

We May Not Reach the Ending by YesThatsMyNaturalColor:
It was a PR event that caused everyone to think of all these tests, of
all these things revolving around the serum and Steve that were shoved
under the rug, forgotten about over the years.

New by misbehavingvigilante:The serum was a blessing really.Really, it was and Steve was in no way trying to make light of all
the sacrifices that went into creating it or from preventing it from
going into the wrong hands either. However it was odd experience when to
date the bulk of his life experiences had spent in the constant throes
of damage and disease to suddenly be bereft of most of that.

In the meantime, In Between Time by nativemossy: Steve was born sickly, and by all realistic means he should have been dead. But he wasn’t, and that was precisely the problem.
He had been born a month and a half early, with asthma, a
heart condition, and an irregularly bent spine, to begin with. That was
followed by a bought of scarlet fever when he was eight, and a brush
with death from rheumatic fever in his teens. These were interspersed
with summer colds and winter flus, sometimes twice yearly. Into
adulthood he had frequent stomach ulcers, and a case of pernicious
anemia that required him to spend a significant portion of the little
money he made on discounted liver at the butchers shop. Had anyone else
had his cocktail of illness, they would be dead several times over.          Yet, he remained, and there was only one logical explanation as to why that was.

Short-Stack and Jerk-Face by MountainRose:
The Enchantress gives Steve a ‘gift’ of the worst kind, but it does give
him the courage to do something he’s been meaning to get to for a
while.

Someone Reaching Back for Me by @festiveferret: Steve is sickly, unemployed, broke, and homeless. All he has left is a business card with a rather hard to get phone number on it.

Masquerade by AnonEhouse: Preserum Steve (I’m going with the comics version,
thin/sickly/tall) meets pre-arc reactor Tony (I’m going with the movie
version-I love puppydog brown eyes).They don’t quite admit falling in love with this other flawed person
who just seems to fit so well… but they don’t quite deny it. When Iron Man and Captain America meet, they fight the attraction
because HEY, I’ve GOT a boyfriend… but… I like you, too. Things get
incredibly complicated, but it all works out in the end.

Smaller Without You by 27dragons: The doctor pulled out the teacher’s chair and sat
across from Steve, his hands folded and his face solemn and kindly. “It
happens once in a while,” he said. His voice was soft and gentle, and
irrationally, it made Steve angry. Such ugly news ought to be delivered
in a more fitting tone. “The most likely cause is that your intended
mate died before you were born or shortly after they were born, before
the bond had time to fully form. It’s called a Type C or a Type–”Steve wasn’t interested in the terminology. “Is that why I’m… like this?” He gestured down at his frail, sickly body.“Probably,” the doctor said. “There are some further tests we can give you, down at the hospital, to determine–”“Why
bother?” Steve growled, slumping back in his chair and crossing his
arms. “My mate is dead and no one else is going to want me, not like
this.” Tears stung his eyes and he blinked them back furiously.“It’s
also possible, though less likely, that you’re a Type A – firstborn of
the pairing – but that your mate has simply not yet been born,” the
doctor said.

Rich Man, Poor Man by sassyfangs13:
Steve grew up in a time when sharing what little you had was the norm so
when Tony starts buying him rediculous gifts he doesn’t really know
what to say.

Provisions by windscryer:
Tony finds Steve up late and for once he chooses talking over doing.

Getting Your Betty Crocker On by thehoyden:
He knows it’s not wartime anymore, but he can’t quite suppress the
twinge of guilt he feels at measuring out two entire cups of white
sugar.