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When it needs it. As you get more experience, you'll start to be able to feel it while you're washing to an extent. You could always use a plastic baggie, put your hand in it and spray some detail spray on the panel and feel for contamination. It kind of just a feel for it that you develop. I tend to do it, even if it's just a quick trip around the truck, everytime I wax.
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Mods
BBK 75mm Throttle Body, AFe Stage II CAI, Granatelli MAF, OBX Long Tube Headers, Magnaflow High Flow Catalytic Converters (#94306), Magnaflow 3" Catback (#15681), Troyer E-Fans, ASP Pulleys, SCT X3 with Custom Troyer Tunes, Pro Comp 1069 18x9 w/ Cooper Zeon LTZs 285/60r18
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