Prefer MMC and perspective, he's the nobody and she's the somebody. Would also love stories of a rich girl/poor boy, city girl/country boy, princess/commoner, etc. Romance, drama, etc. Nothing that goes on forever, no harems, I am looking for one on one relationships.
The Unicorn by qhml1
Romantic
Part of Women Power
An average guy. A retired model worth millions. Can it work?
Still can't find the one I'm thinking od but here is another.
I'm on My Way
Broken Hearts
by dangerouslydead
Jay Cantrell has some others as well, the two stories under https://storiesonline.net/series/1279/regan-riley-and-andy-drayton would fit some of your criteria.
Regan is not particularly well known, but very very rich.
Andy is living in poverty when the series kicks off.
Moving away from those two and onto Don Lockwood,
https://storiesonline.net/s/40269/finding-a-place and
https://storiesonline.net/s/40267/transcending-the-role both fit.
Finally, one more from Argon - and with a twist:
https://storiesonline.net/s/22004/suddenly-rich-kid (the twist being that the star does not get the girl).
Love that story just want it to be much longer and more dramatic. I want it to not be a story he tells his students but for us to be right there as it happens. That's the type of story I want
Not sure about that one, Phil may be rich but he's so well known that one other student (a baseball player he grew up with) actually knows who he is. Then again I suggested Andy Drayton / Regan Riley above and Regan is not that well known either.