@Steven_Keller thank you for your help. Well my dirty secret is that I am not waiting on a response through a dump_socket. This was another issue I worked there where when I was waiting on a response it was taking ~65 seconds (Ubidots forum post regarding this).
This may have been a fatal mistake that could have lead to idneitfying a root issue, but at the time I was willing to do anything just to get the thing to send more than 3 times in a row!
I am going to go back to basics and go back to this tutorial to try and wait for a response again and see if I get the same results between the Hologram SIM and the AT&T SIM.
I am also going to to look into what it will take to move over to MQTT, thank you for this suggestion.
UPDATE: It appears the AT&T SIM is now acting up in the same way as the Hologram SIM (missing data). Based on your feedback and these new findings I am thinking the root issue is in the connection protocol and not the cellular side of things.