This always seems crazy to me. Obviously depends on what airline you're flying, where you're flying from, and how many different possible routes there are...but still. If nonstop flights don't look good and you keep missing, fly somewhere else and try from there. In all the times I've flown standby in my life, I've never been "stuck" anywhere for days. Never even been delayed by more than 12 or so hours. I guess maybe I've just been lucky, though.

For instance around Christmas/New Years I was trying to get back to LA from NY. Was planning on leaving Sunday evening straight to LAX, but the two late flights were full. After missing the first one I decided just to go to SFO instead because there were seats there. Got in too late to catch the last LAX flight, so spent the night in the airport and was going to take the first flight in the morning. Come morning that flight wasn't looking too good and later flights were iffy, so decided not to chance it and went to SAN instead. Got in by about 7:30 am and just rented a car to go the last couple hours north. Was a bit dicey and had to take a crazy route to get there, but in the end it was less than 12 hours later by the time I got where I wanted to be, and didn't cost anywhere near as much as buying a last minute plane ticket for a transcon during the holidays. Or a hotel room for multiple days. Even the one way rental was just little over $100.

The most important things you need if you're going to fly standby are time, patience, flexibility. Also, don't fly standby if you're going somewhere you absolutely have to be. If its just a last minute weekend trip for fun, go for it. Sometimes the craziness and uncertainty can even add to that.