Thanks for everyone's updates and work looking into this problem.
Could it be due to the firmware upgrade on the pineapple itself? I am running 2.8.0 I upgraded the firmware using a clean install (Serial TTL). Also, as hard as it is to conceive, could the formatting of the SanDisk 4GB cause this as well? In an effort to install user packages (such as auto Rickroll, etc.) by default to the USB and not the pineapple, I followed Derek's instructions on the forum. This allows the pineapple user to choose between installing on the pineapple or the USB.
Could this formatting have something to do with why the USB is not powering up through the USB power adapter? I have no idea, I am just throwing out any and all possibilities.
Thanks again for the continual hard work guys! We all appreciate it!
-G