After exhaustive troubleshooting and testing I was able to get PortalSmash to work with my code. After stopping the Kismet server to post the results of the collection, the bash script opens PortalSmash (a ruby script) in a new window. I modified the PortalSmash code to exit if it successfully establishes a connection over a known or open network. The bash script saves the PID of the newest bash process as soon as PortalSmash launches and so if the script doesn't close in a certain amount of time, my bash script can kill it and resume Kismet again. Brendan was really nice and eager to help me troubleshoot and I'm excited to share this project with him when it is closer to completion.
I have ordered a GPS receiver and it should be here tomorrow afternoon. I am using the GlobalSat BU-353-S4, the same receiver that was listed in the SANS Institute WarPi documentation. I considered using Adafruit's Ultimate GPS Breakout but decided to go with a plug and play solution. I also like the look of their GPS Antenna but it draws quite a bit of current and I don't know if I will need a gain boost yet.