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I don't quite understand the point of this "hit point" system when the emphasis is on creativity and adapting to the situation. The player asks if they can do something – the GM immediately answers whether it's possible (although they might conceal it, of course), deciding for themselves how many uses are needed (if the effect will even work). Hit points are a completely foreign concept here. They would make sense, for example, if the player wanted to knock a chandelier onto an opponent with an arrow (and then the GM would have to figure out what and how, if they haven't already devised a system for such cases), but not here.
Maybe. Or maybe it would be too far-fetched, even if you don't evaluate things like columns using the standard enemy system. No, I remember, I've already shown similar creativity with you before, when we threw bombs at the undead giant with a crow. In principle, I was satisfied with the result, so...