You just have to look at this a different way.
Among serious frequent flyers, what you have here is called a "mileage run." You have all these extra legs, and it's costing you much less. You just are using those to rack up extra frequent flyer miles.
Some of the real fanatics specifically book this kind of insanely complicated long itinerary just to gain miles and status with the airlines. For instance, Buffalo-Detroit-Atlanta-JFK-Atlanta-Minneapolis-Buffalo. Some frequent flyers would seek out this itinerary because all the segments and miles would raise their tier status on Delta.
Some flyers have been known to do elaborate trans-atlantic mileage runs where they get off the plane in Stockholm or wherever, and then get right back on it for the return trip. No point to the trip whatsoever except to earn miles and status.
I worked with a guy who did this sort of thing with a friend of his. They'd find discounted runs to wherever and spend weekends flying back and forth to God-knows-where solely for the purpose of racking up mileage. Then, during their vacations, they'd turn the miles in and fly to far-distant foreign lands where they could spend their money on the fun stuff rather than on getting there and back. On occasion, when they'd fly hither and yon they'd spend a cheap night at a hotel that offered "points" and was affiliated with someplace they could stay in wherever their next "big" destination location was, thereby avoiding the cost of lodgings, as well. They had some fabulous vacations, but I couldn't imagine the work it took to find the best bang-for-the-buck weekend flights, nor how mind-numbingly boring those weekends must have been (and I love to fly). That was all far prior to 911 and Homeland Security, though. If I thought it was a nightmarish way to spend weekends, then, I can't imagine the horror of trying to do it, now.
While I didn't go to these lengths, I will admit to taking an "unnecessary" flight once or twice to maintain my elite status, too. I usually went to someplace I wanted to go, though, even if it was a day trip, rather than to random "anyplace cheap--it's okay if there's no public transportation and nothing within 60 miles of the airport" destination like these guys would do.
