Moss you will need all 18 1/16" bits to drill 40 pilot holes horizontally. I would try 3/32" pilot holes minimum, see if 3/32 survives or 1/8, then go to 1/4". Note: that's 80 holes. You CAN lube a horizontal drill bit. If you go to Home Depot and buy a Milwaukie 1/4" bit I would expect it to drill more than 40 holes in normal angle iron and still be sharp. Something is way wrong if its dull in 2 holes. The 1/8 bit can spin fast. The 1/4" bit should turn about half the speed of the 1/8.
Tallyho8 you should probably tip that trailer up - block the wheel up a foot or two & save your back.
Easiest and fastest way to drill horizontal holes is with the annular type bits such as Blair / Hougen. They are like holesaws, they are fast because they don't have to turn the whole plug into chips. Great for battery drills, they cut faster and with less power.
Among the best $63 I've spent on bits was this kit by
Blair, but this kit doesn't have 1/4". It has 5/16, 3/8, 7/16, 1/2, 9/16, 5/8, and 3/4. Maybe you can use 5/16" holes for your project.
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