It's all or nothing for me. If you are going to prioritize his health, you listen to his doctors. If you are going to prioritize winning now, you go all-in.
I haven't read one compromise plan that looked like it wasn't risking his health nearly as much as just throwing him through October.
If you had followed an ebb and flow system with his starts, I think you could have racked up something like 15-20 innings for the playoffs.
By this I mean a 6/5/4/4/5/6/5/4/4/5/6... type of innings work load.
I never worked out the math... but if you follow that type of schedule, he'd certainly have some innings left over for October, provided you make it there.