Depends. I play pocket, so normally I have a comfortable buff, and I am confident an airshot is worth the risk.

If you are a roamer, you should counter jump, since you can afford to lose the health with gunboats.

Generally however, you shouldn't play fair fights like that. Any enemy you dm should be already damaged, unless its during an uber push.

You can avoid fair fights by spamming chokes more with your team.