Could the case for my iPod cause a problem?
It's possible! The iTripLCD with dock connector MUST be completely flush with the bottom of the iPod. Most iPod cases, even ones with pass-through slots on the bottom, will most likely prevent the iTrip from fully seating properly, which will prevent it from receiving power.
Unfortunately, due to the shape of the 4th Generation, 2nd Generation iPod Nano and 2nd Generation iPod touch, the opening of the iClear and Reflect could not be flush with the bottom of the iPod. For this reason, the iTrip Dock cannot be used without removing the case first.