I don't know the bloke, don't have a dog in the fight, but here's my view fwiw: he works inside the football media, in a rapidly growing sector and has regular access to people who know things in the game, whether they be on the footballing or journalistic side. Quite a lot of those people speak to him regularly so they build up a rapport. They're also being paid, I assume, for their contributions, so they'll be quite happy to discuss things with him both on-air and also, I would suggest, off-air. I don't think he holds himself out as being a super ITK or anything but he does appear to be someone with contacts within the game and also senior contacts within the club. Football is one of the most gossipy professions going. Like all people who work in an information sharing field he'll sometimes be told something that isn't the case, or something that isn't true and people will hammer him for it. Journalists who've been working around the club for decades can't get to the bottom of the story conclusively. Some of them have different views and/or sources of information. If they can't pin it down beyond doubt what hope for anyone else?
So, yeah, I'm sure he gets things wrong at times. I also know he gets plenty of things right. That doesn't mean that when he tweets or offers an opinion that it has to be through the prism of being the Internet's favourite ITK, with a mole in every boardroom. In fact, I'm pretty sure he himself has said he's not holding himself out as some top level journalist who has a line on every story. Those people don't exist. Use the Caf's favourite, Di Marzio, for example. Ask yourselves what you actually believe the extent of his 'powers' are. It's like trying to figure out the logistics of how Santa could deliver gifts to every child in the world in one night.