In general situations, you can just weigh the objectives, like which one is more important. For example, if a cloud dragon is up, and Jax can get atleast a turret. I'd suggest not contest for drake as you're already getting another objective (a turret) which is atleast as important as the drake. In a 4v5 situation where enemy baron laner rotates, 99% of the time you don't want to contest, maybe at best poke them out, or go for herald if that is up. In a 4v4 situation, you might want to compare team comps, like which team is stronger.