However, I’m often scared about how much people talk about how “improvising” (in the broader sense) is so crucial to the game. It’s fun doing that, but you don’t actually need to do crazy stuff all the time; often the simple choice is best. When the simple choice really is the best, going into risky overcomplicated feats, involving several checks seems like being a show-off here. However, if you do get advantage, or even save the day with that, you’re a hero. I properly reward players when they have a good idea, but not every idea is a good one.
I agree that too much "crazy stuff" is not good (with the definition of crazy being unique to each group), especially when it takes up a lot of time to resolve. But, when a great tactical plan comes together, with mostly standard rules leavened with some unusual ingredients, it creates a memorable session.
In my games, combat "improv" usually comes down to using existing abilities in unexpected ways, making use of the environment, or role-playing to gain advantage or distract a foe. (Often this doesn't amount to anything more than some good verbal repartee during battle.)
I like things to keep moving and stay "realistic" within our genre expectations, but I definitely want enough creativity for battles to feel more interesting than a long string of rolls to hit.
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