I'm curious as to why US 64 has the indirect routing to Haskell (via US 169 and Memorial), instead of the more direct path along SH-51 and SH-72...
Because of the Arkansas River. The road that is now OK 72 wasn't on the state highway system in 1926. I'm guessing there was no bridge there at the time. There's been no reason to change it.
A possible rerouting of US 64 could follow OK 67 from Bixby Kiefer, then US 75A from Kiefer to Sapulpa, and OK 97 from Sapulpa to Sand Springs. This would bypass Tulsa but it would be faster to take the current US 64 routing. But as I said, there's no reason to change it.
I believe US 169 should be extended south across the Arkansas River as a freeway that would end east of the Leonard Curve. Memorial/US 64 between the Creek Turnpike and south of Bixby is awful during peak traffic. This freeway could be extended to meet US 75 somewhere between Tulsa and Okmulgee or even towards Muskogee.