Wow, my calculations were way off!
Here is the correct amount of miles for each option.
All flight options are $97 all-in.
Upgrades are always nice...
737-700's have 12 F seats
737-800's have 16 F seats
777-200's have 50 F seats
Of course on the other hand, the larger the plane the more elites there probably are.
1.
PIT-IAH, 5:52pm-7:55pm, 737-800, 3:03 duration
0:55 layover
IAH-SNA, 8:50pm-10:25pm, 737-800, 3:35 duration
Miles=5,542 (1.75cpm)
2.
PIT-CLE, 1:05pm-1:59pm, Q200, 0:54 duration
0:46 layover
CLE-IAH, 2:45pm-4:44pm, 737-800, 2:59 duration
1:21 layover
IAH-SNA, 6:05pm-7:39pm, 737-700, 3:34 duration
Miles=6,608 (1.47cpm)
3.
PIT-EWR, 12:37pm-2:24pm, Q400, 1:47 duration
2:36 layover
EWR-SNA, 5:00pm-8:08pm, 737-700, 6:08 duration
Miles=6,599 (1.47cpm)
4.
PIT-EWR, 12:37pm-2:24pm, Q400, 1:47 duration
2:06 layover
EWR-IAH, 4:30pm-7:06pm, 777-200, 3:36 duration
1:44 layover
IAH-SNA, 8:50pm-10:25pm, 737-800, 3:35 duration
Miles=7,337 (1.32cpm)