I can understand the sentiment behind why he did it, but… I really think that was a bad idea.
As a pilot myself, you always need to ere on the side of caution. Sure, a jumbo jet is made for resisting a lot of weather conditions, but that close to a hurricane? The potential for wind shear and clear-air turbulence is amazingly high. I don't know if it's different for high-altitude, IFR-rated fliers like airliners, but as a helicopter pilot we're trained to never try and "thread the needle" between storm clouds. For one, those clouds could close, and for another, just because there's no clouds on the doppler doesn't mean there's no conditions there.

Of course they would be stranded on that island, but unless that really was their only choice rather than hunkering down in a hurricane structure, I really wouldn’t stand behind it.

A heroic move, but incredibly risky.

…did we ever see Poe from The Force Awaken do any actually impressive piloting? from what we saw, he crashed a tie fighter, shot a few guys, and didn't really fly anything other than that. I think. I can't remember his role in the movie that much,

…but yeah, wholly shit that takes skill. And a stupid about of bravery