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Is drilling and tapping the oil pickup boss to 1/2" still a common practice on street/strip 440's?

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No It was and is a bandaid to help correct other things in the oiling system Get the bearing clearnances right, not to tight, get the pressures and flows correct and use the correct modern oils, not to thick You'll be golden Oil needs to flow to do what it is designed to do, lubricate and cool the contact surfaces on rotating and recriprecating (SP?) parts

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At what performance level is an external pickup considered mandatory? What is the best external setup?

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Any motor I build that will be shifted above 8000 RPM would have a good external oiling system on it, preferably a dry sump system My current low deck stroker (505 C.I. 400 block) bracket motor has a Milidon pump and dual line oiling system with the swinging pick up in the Charlie SS style fabricated aluminum oil pan, Charlie extended the dual line Milidon swinging pick up for that oil pan.I used it, the sytem, because I had all the parts hanging on the wall and on the shelfs It, this oiling system, has NOT given me any problems (like no oil pressure on start up after sitting for a while ) since the motor was built and dyno tuned three years ago Unlike some other dual line Milidon oiling systems I have used in the past