Any problem with drilling two additional drain holes in the very front (cab end) corners of my 2007 Silverado 1500 Crew Cab truck box? Wouldn't want to drill through the box and risk hitting anything vital. Plan to use a 3/8 inch drill bit.

 

as long as you have clearance underneath. have a look and make sure the drain hole is not over a connector and will drain into a part that holds water. primer and paint the holes.

 

I wouldn't it. I want my truck bed solid. If you go to sell it, and the buyer spots it, you could lose a sale. That and you might promote rusting at the holes too.