I forsee travel in my future

In light of the current economic situation, I'm going to be moving and helping out my aging grandparents rather than continuing to butt my head up against a scarcity of jobs I am neither over- nor under-qualified for. This leads directly to me looking at air-fair rates. I think I complained about this last time I moved, but it's annoying me again so here goes again.

My starting point and my destination are both major hubs and I could get a direct flight between the two of them. Why would doing so cost THREE TIMES AS MUCH as flying past it to the coast and then taking another flight back? Why (and I checked on this) would taking a two flight trip that used the straight shot from here to my destination as one of its legs cost A HUNDRED DOLLARS LESS than just leaving the airport at that point? If I could get away with only having carry-on luggage I'd be tempted to just "miss" my connecting flight...

I understand that you pay more for convenience, but that is ridiculous.