The way I look at it, you can always *try* getting to your destination. Worst case scenario, you go back home. What you really need to plan for is getting back home. If you don't make *that* flight, you don't get back to work on time. Then again, I think that getting home is easier, at least in some locations. For example, when I wanted to go from MSP-HNL with a stop, I could choose between SEA, PDX, LAX, or SFO. Getting there, I had to be really careful about what I chose, since flights to HNL are... well, I shouldn't even have to explain that one. Choose the wrong one, and I'd have to turn around and go back home. On the other hand, I can get back to MSP through any of those 4 cities (there's also a nonstop, but that's REALLY tough). However, if there are several maybes, and they all left around the same time like they did, I could take the first flight back to the mainland I could get on. From there, I can eventually work my way back to MSP. Even if I have to do a really funky routing, like SFO-DTW-GRB-MSP.
That was a really important suggestion I learned from a coworker when I first got started, actually: "If you can't get a nonstop from somewhere back to MSP, always go to Detroit. You can always get to Minne from there. Just be prepared to make a halfway stop, like in Madison, Milwaukee, Chicago, etc." Sure, it makes for a long day, but that's half the fun with this stuff.
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