Now, this is an awful idea which nobody is ever going to try. But as a thought experiment, consider the flight STT-SJU. It is an AA flight of only 68 miles. It's a cheap flight(I'm looking at about $56 each way on some random sampling), but most importantly, it's the shortest flight I could find. Better yet is STT-STX-SJU, which is 94 miles for two segments, but for some reason you cannot book STT-STX or STX-SJU individually.
This gives us a miles/segment amount of 47 Miles/segment.
Now, you might not know much about AAirpass, but it is a full fare system in which you buy at least a $10,000 block of miles (I believe it is 40 cents this year per mile, which I'll base the calculation off, but there are no good sources on the accuracy; I've also heard it's up to 50 cents this year). Booking a flight is based off the distance flown and class of service: flights cost a number of miles (at 40 cents each) equal to the distance, with a penalty for short flights and a bonus for long flights. For our STT-STX-SJU, multiplying the mileage/segment by the 1.35 penalty for a sub 500 mile flight brings us to a cool 24.44$/segment, or $2444 to qualify for EXP. You just have to fly the same route for 100 segments. In addition, the 500 mile minimum(for elites) gets us 100,000 miles, which isn't bad.
So, supposing you have a corporate AAirpass split across several people, this insanely foolish strategy would give 2.4 CPM for our RDM, in addition $2444 per EXP qualification.
Finally, supposing there are any shorter AA flights I've missed, it only gets better. If there were a 20 mile AA flight, you could get EXP for only about $1000 per person and get the same 100,000 RDM at ~1 CPM.
Anyway, this is a terrible idea and nobody should ever try it, but I thought it was a cool thought experiment. If I missed something (such as an Aairpass minimum cost on short flights), then I'm just right off, and I apologize.