I use the McMaster knife edge threaded ones (steel not "pot metal") that install w/ an allen. I cut a short piece of allen wrench & put it in my Makita. so I could push on them
The ones I used weren't stainless, I put them into MDF, did the trial & error thing.
I think the od of them was close to 1/2" I think I used 7/16 or maybe
32nd less than 7/16. Bigger pilot hole IMO is better than too small, less apt to rip up the wood upon installation.
If your insert is the SS slotted drive one, they suggest a 3/8" drilled hole; mihgt be a little tight for oak
here's the insertt info
90192A124 Hi-Strength Stl Knife-Thread Insert for Wood Hex Drive,
1/4"-20 Internal Thread,
25/32" Length hr bar Type Knife-Thread Inserts for Wood Material Type Steel Finish Plain Steel Type High-Strength Steel Drive High-Strength Hex Drive System of Measurement Inch Internal Thread Size 1/4"-20 Insert Length 25/32" Drill Size 3/8" Hex Key M6
cheers Bob