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You can't choose the same target more than once for a single strive spell

It is still more than fine when you only have one thing you can take, even if it isn't that great of a card

That combined with plenty of other low toughness creatures to make Serrated Arrows an amazing card, and often the other player would have no choice but to lose three otherwise fine creatures to the Arrows

I recommend you use something like this to check for over/under extrusion

Discussing the merits of Despise against Harsh Scrutiny however is more pertinent

If Reluctant Role Model dies at the same time as one or more other creatures with counters on them, its last ability will trigger for each of those creatures