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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Thank you for the excellent article! Having acquired an 18 year old boat a couple of years ago and almost never hiring out for repairs and maintenance I have struggled with several of the things you mention here. The methods you discuss are sure to help me on future projects. FYI, I figured out the method of using a drilled scrap of plywood as a template to drill a larger hole while replacing my deck mounted windlass switches on my on. I was very proud of the results! You definitely have to be resourceful if you own an old boat and are not wealthy.
The Sailrite guide looks suspiciously like an electrical ground clamp meant to attach a ground wire to a water pipe. Amazon has one for $7. Search “ground clamp for wire”. Not exactly the same.