Midway is still somewhat easier than O'Hare, but not like it used to be. I avoid the whole mess by parking on the other side, by the Orange Line train entrance, in a parking lot that is so close I can walk rather than deal with shuttle buses.
I know what you mean about the short runways. On ATA, I often sat in the exit row across from the jump seats, and on the massive 757-300s the FAs taught me to look backwards while landing...you can actually see the plane fish tail as they brake it! It's not so apparent with smaller aircraft. And once we had to abort our landing at the last possible minute due to a sudden tail wind. I'm sure it's routine for the pilots, but it always gives me the willies.
I am a very paranoid flyer, and like you, I want to know where my seat is. That's why it's taking me a while to get used to Southwest, but for the price I just can't justify one of the O'Hare carriers (by the way, we're one town south of you!).
Barb