It's not a big deal to launch into the face of something like that as long as you've got a whole bunch of good alternatives if it doesn't work. I flew a Charlotte to Freeport flight in 2011 just as Hurricane Irene was running in to the Bahamas. They gave us enough gas to get there and back (twice!) and we were supposed to get in just about 45 minutes before the outer bands of the rotation started hitting the island. We managed a 30 minute turn and took off with blue skies but a huge hurricane bar just to the east. We took two mechanics with us to QUICKLY solve any problems that might have came up. Total non event. Storm location forecasting is pretty good now and you can always turn around (did that once in 2009) too if it doesn't look good.