One of the best resources I found for explaining exactly how the guardian system worked is actually a 40 page pamphlet available for free. Even more miraculously than it being free, it’s written quite clearly. I find a lot of sources from the time have an overwrought style that’s difficult to follow. Released in 1924 by Gertrude Bonnin and the Office of Indian Rights after a trip to Oklahoma, it’s available here as a pdf.
Gertrude Bonnin is also known as Zitkála-Šá, and was a Sioux writer, editor, musician, teacher and political activist. In 1913 she collaborated to write the first Native American opera, The Sun Dance Opera. She co-founded the National Council of Native Americans in 1926 and served as President until her death in 1938.
Here are some books that sounded extremely promising, but I unfortunately didn’t have the research budget to purchase. If you’ve read one of them, let me know what they’re like.
The Underground Reservation: Osage Oil by Terry Wilson
And Still the Waters Run: The Betrayal of the Five Civilized Tribes by Angie Debo
Osage Oil Business by Kenny Franks was recommended, but I can’t find a copy of it anywhere. Kenny Franks, however, appears to be a historian who specializes in oil business history in the area.
He also edited a book called Voices From the Oil Fields, which is a collection of early oil field workers’ recollections collected by the Federal Writers Project in the late 30’s. If you’re interested more in how the rough necks did the actual day-to-day job, this would be a gold mine.