Hi Brier_Raider,
It looks like your program is off to a good start. The demo provided above is a good place to start in understanding shift registers.
Attached below is a weird way for me to provide you with an answer, but as you said, sometimes an image is worth 1000 words. What I've done is taken your image, and modified it in paint. If you want to count the number of times that case within your case structure executes, you will want to wire your VI similar to that in the picture.
When the integer enters the case structure, it will increment if you are executing the True case. If it is the False case, we will pass the wire through without modification.
The shift registers will be on each side of both the inside and outside while loops, and will store the current count value in each loop's iteration.
Its a crude image, but hopefully it delivers the message.
Robert