Those conditions don't look too awfully bad, beautiful footage. I too enjoy flying in a low cloudy rainy environment, within reason.
There is a reason though that the dire stats exist for VFR flight into IMC. Often it works out fine if everything is pretty static weather wise; you can just fly around, poke your head in and retreat if you have to. But I had a situation one time while trying to land the coast here in Oregon where it closed in around me as I was descending lower and lower to stay under it. The next thing I knew it was on the ground over there --> and I was looking back <-- there for a way out. It was changing rapidly all around me and I got lucky to retest back to the place I hoped was still open. On the coast, if you're an half decent instrument pilot you can just point it toward the open ocean and commit yourself to gong IFR. But if you're a noob VFR only pilot, or hell any pilot, doing this close to terrain and it closes in on you, things will get exciting in a hurry.
Gump has 25,000+ hours, and it's true that not much ruffles his feathers but he does enjoy a bit of cowboy bravado in his tales and jokes on this site. He didn't survive all those years in shitty weather Alaska by being reckless or stupid.
