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The first context is indeed a context of doing. If "letting be" happens in a context of doing, it would manifest as something he does - letting be like tolerating / permitting / allowing. That's but one tiny aspect of where it's at with him. Listen: even if that were all of it, it would be pretty darn great. How many times would you have avoided a world of hurt if instead of reacting like a tightly wound clock spring, you'd simply done something bigger - like letting be? That would've been pretty great, yes? Yes, except that's not the context for "letting be" to which I'm referring, the context which makes this quality of his so remarkable.
The second context is a context of being. If "letting be" happens in a context of being, it would manifest as something he is ie as something he be's (if you will). If he wasn't doing "letting be" and instead his being was letting be (look: that's a very subtle distinction, the distinction on which this conversation pivots), that would be remarkable - totally extraordinary in fact.
Essentially, "letting be" in a context of being, is having everything show up exactly the way it shows up. So in this context, characterizing it as tolerating / permitting / allowing actually trivializes it. In this context, there's no doing involved. This context actually precedes any and all doing ie it's prior to all that. Furthermore in this context, whatever shows up, shows up in the context of who we really are. That's mastery. That's a master. "Letting be" in a context of being, allows anything (and by that, I do mean absolutely anything) that shows up, to be, without diminishing, diminuting, or distracting from who we really are, nor from whatever shows up.
On the other hand, "letting be" in a context of doing, requires intervention by who we really are. Be careful: one context is neither worse nor better than the other. In mastery, any and all arrows in the quiver are available and useful. Each of them can and will be used appropriately when required. What's important to get is that one "letting be" is an experience and the other "letting be" is an action. Mastery is a function of experience, a function of being, a function of context. Masters of action (as you may have already noticed, even if you haven't put this language to it) aren't always also masters of being (consider the human experience calls us to be both).