You want to size the bone to the dog. A chicken wing for one, chicken back with pelvis for another. It should be big enough that the dog won't just swallow it, but obviously should not outweigh the dog. He should be able to eat the bone, or at least make headway where you find teeth marks.
Round bones may become lodged around the lower jaw so make sure the marrow hole is big enough. No beef leg bones, too hard.
When he walks away form the bone put it in the refrigerator. If you keep it refrigerated in between chew sessions it should last three days. After that toss it.
Milo has never walked away from a bone! Lol. But I also give him appropriate portion. He could probably eat an entire chicken leg but he gets a skinless drumstick instead. Duck feet, pork rib tips, chicken back, chicken wings, turkey wings. I don’t give beef bones, but when I have some game meat, I do get milo to chomp on the part where there is a ton of sinew, so it acts like floss for his teeth but not on the bone itself.
I don’t give my dog raw bones and no cooked ones either. My vet has seen too many dogs with broken teeth. Mollymuimu’s dog had eaten bones regularly until she broke, I think two teeth. Required surgery to remove them because it was painful. And she’s very careful with Molly. No more bones for Molly.
I also never give my dog reindeer antlers or anything else too hard. I stick to safe chews like pizzle sticks.