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I've got blisters on my hands from taping 20 holes manually and I have
hundreds left to go!
What machine or tools do I need to tap 5/16th-18 holes in aluminum? I
am using T slotted 1.5" square tubular aluminum for a lot of projects,
ranging from a workshed to a photobooth to a workbench and having to
manually tap the ends of this metal is going to kill me! I'm
specifically using http://www.8020.net/T-Slot-1.asp this stuff. I
bought two specialty taps that are a combination drill/tap bit from
www.mcmaster.com part # 2748A43 At $20 each they are pricy and I've
already busted them both after only about 6 holes each with a hand
drill.

Any help please?

You need a drill press and a small Tap-Matic, or drill the holes and use a
hand tap. But why do you need to tap so many holes? Usually the point of
T-slot is that you can use special "nuts" that slide or tilt into the slot.