I think most of this is because being entertaining is something that Phil would be responsible for. He fears basic concrete change, nevermind the level of introspection, empathy and hard work it would take for him to figure how to be entertaining. Phil HAS to believe that the hot games are going to bring in the views because that is all he can do - pray for some external salvation. Not only that, but looking to games lets him externalize the failure - shit sucks because the games suck. If he was trying to be entertaining, that's when he'd have to cope with the fact that HE sucks. He can't handle that.
Another part of this is Phil is looking at the wrong people. He keeps referring to big Youtubers or internet celebs who occasionally pick up the hottest game and stream it, which is only a fraction of their content. Phil covets their wealth. The type person he should actually be looking at is someone like Dansgaming, who plays new releases, but can also pull in thousands of people while he replays Morrowind on some random week in 2018. Dan is a better model for Phil because Dan makes his living exclusively from Twitch streaming, and he doesn't act like a muppet to be entertaining. But while Dan is doing well, he hasn't got the wealth or life of luxury of the people Phil tunnels on, and so Phil sees "Hot games make you a millionaire!" All while neglecting that he long missed his chance to be like those people because he doesn't do anything else.