I've been traveling for work the past couple of days and haven't been able to respond but I have an update.
I knew my BF and his boss at the car dealership weren't getting along for a while. He told me sometime last week (after I created the original post) that his boss tried to stiff him on the commission of one of the cars he sold, so he quit. Meanwhile, he'd been talking to a friend (former bad boy) about another opportunity, so he decided to pursue that. It turns out that this "opportunity" consists of him recruiting people to do door-to-door sales, selling Comcast products. The position is not through Comcast, it's for a company contracted by Comcast.
If I had any doubts before, I knew at this point that it's over. Right, wrong or indifferent, I have no desire to be with a door to door salesman. It's not in the direction that I'm going, and it's not in the direction of a true career path for him, either. The subject of going to school seems lost at this point. I saw a glimpse of what my future would be like with him (especially if we ever had children), and I know that's not the life for me.