Poking a ⅜-in. bit into wood is simple enough. Place the bit on the mark, sight the drill from two directions at 90 degrees to make sure it is straight, and drill away. A hole in flat metal plate is simple enough, with the added step of center punching the mark to discourage the bit from wandering. The center bit of a hole saw will guide it true. But there are trickier cases, where the drill wants to wander everywhere but where you want it. They all have simple solutions.
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