Drilling stainless steel can be a pain in the you know what. My maintenance guy says Winzer Shop Pros do pretty good.
It just plain sucks drilling stainless steel on a regular basis, especially the good stainless mostly because it heat-hardens more so than the milder grades.
The biggest problem is most people try to drill stainless steel with way to high of an rpm and not enough pressure.
The keys to drilling stainless steel.
-> Lower work speed.
-> Higher tool pressure.
-> Lubrication.
-> Keep the bit cool. (air stream on it or compressed air)
Possibly pilot holes would help.
2013 EC Silverado aka redruM (Just a couple bolt ons.)
2007 RC Silverado aka ?
1998 Trans AM aka Red Dragon
"Your pull your truck to the track on a trailer, I race you with a truck that pulled a trailer to the track."