Amazing suggestions and solutions.. Thanks folks! I was able to take from this and come up with the ending I was hoping for. If you'd like to give it a shot, you can find it searching for "monjon1" :) Thanks!!
This works, but sadly, you can't branch the actual story objectives off. So a new "Speak to" objective couldn't differentiate between one NPC or the other and two separate "speak to" objectives would each have to be completed to keep going.