Wow,
I am always amazed at the "mystery" about how casino's are run. I can recall many different cases of somebody doing exactly what I mentioned in my earlier post. People will try and scam as little as $5, if they think they can get away with it. As far as the dealer or "pit boss" getting in trouble, look at the pecking order. Another point about all those camera's.....when actual people use to be in surveilance the chance of getting away with any type of scam was less. Mainly because proof didn't have to be provided to 86 or "rough up" a customer. Now you have to catch the person and have video proof before any action is taken. This requires many hours of going over the video, hoping you have the right angle, or even having a video. Not all camera's are on at all times!
Back to the purchasing of roulette chips......another option would be to ask one of the higher ups (shift manager) to help with what you want. Sometimes they will take you right over to the table and let you purchase any amount you want. A recent example of this was I put together a nice framed picture of all the Douglas County current casino's with pictures and chips for an auction at one of our Nevada elected official events. They not only helped, some of them just gave me the chips I requested! The downfall to this would be if they say no, you would have to wait till they are gone to try getting the chips by yourself.....worth a try.