Strangely I can do a quick run from this screen

But the run button the this screen isn't clickable

I think I have my answer, you are able to create a deployment (at least via python) that does technically deploy but does not satisfy the conditions for that run button. I suspect the fact you can do a quick run via the other menu is a bug This seemed to be resolved by adding the

upload=True

argument to my call to

Deployment.apply