He's putting a lot of time into something that is feeling more and more like smacking himself in the forehead with a ballpeen hammer. I have no doubt at all that if he sticks with his writing long enough, he'll start selling his work. He's smart and talented and funny, and I think it would be impossible for him to keep writing without those qualities showing in an irresistible combination on the page eventually. Sooner or later, an editor is going to fall in love, and he is going to find a publishing home. If he is willing to pay the price.
Every dream has a price.
You need to know this now, because the price can be enormous, and if you don't know about in advance, you can wake up one day to find that you have paid with everything you ever loved, and what you have to show for all of that isn't enough. There's no way you can know in advance. You might have to live in poverty. You might lose your job, your friends or family, your children or your spouse. Your dream might cost you your health.