The term "Shadow Games" is associated with the term "Cloak & Dagger", and is usually used in connection to some sort of spy or espionage-type activity. Misdirection is a key component, and (as any James Bond fan could tell you) it may involve making one action appear to be a different action.
In this context, Kip is suggesting stealing one car from one area of town, another car from another area or surrounding town, etc..., not on the same night. Spread it out. Don't let anyone recognize there's a pattern. Case out the cars (which they do for one Mercedes, actually), make careful decisions on what the easiest targets are.
Memphis, on the other hand, suggests the polar opposite; get them all on the same night, as quickly as possible, before information can be exchanged by law enforcement. Grab and go, and let your driving skills get you out of trouble.