Well I thought a little bit more about someone else's comment about all the time spent on the flights, and if I really wanted to spend time in Las Vegas (at least one of the two times I was going) I think I would have gone with the itinerary. But since I don't I think I found the cheapest and quickest way to get ten segments:
PIT-ORD-BNA-STL-DFW-IAH-DFW-STL-BNA-ORD-PIT
A lot of these segments are on props, all are in coach, but each segment is only about an hour long, and I was able to do it in two days (overnight in Houston), leaving 9am and arriving back at 10pm. The EQM drops to basically the minimum 5000 miles vs the 9900 I was earning the other way, but the price drops $400, so I think its a good tradeoff, for my situation.

Thanks for the feedback, it did help me put it into perspective!