He has never worked for Disney AFAIK. He's an uber-fanboy. Years ago on his blog I think he mentioned that he tried to develop a screenplay based on Haunted Mansion. So he's a wannabe screenwriter or a one-time fan-fiction author or something.
He seems to have one or two contacts with people who work for Disney which is where he gets his rumors. Or maybe he only knows people who know people so he gets it second or third hand. But I think that most of the Disney history stories he tells are based on public sources ... books about Disney history, interviews and reminiscences of Disney legends, etc.
Lately he's also been invited to journalist previews of attractions and restaurants at Universal and I got the impression from listening to the way that he described these events on the podcast with Len Testa that his usual M.O. is to lean heavily on publicly available information, but to present it in a confidential tone that implies that he's got the real inside dope. He's not misleading or dishonest in any way, it's just his natural excitement and pride at getting to go to these things and hear the stories.
These are only my impressions from reading a little bit of his stuff and listening to him occasionally. He's an entertaining guy but you have to try to parse what he says to try to figure out where he gets his info. Part of the obfuscation is hucksterism, part of it is trying to protect his sources ... assuming he has any.
I wouldn't worry too much about anything that he says about the future, except I'm kind of curious (like everyone else) to see if he called the DHS story correctly. Basically he said that some concrete additions to
Pixar Place will be announced shortly, but that yet again this year, only vague generalities about "big things" will be announced about Star Wars in DHS. He implied that the people concerned with this are embarrassed at the lack of progress but the blame goes back to the board of directors for tearing up all of their previous proposals/plans. He said that the Disney spin on this is, "it's actually good news ... they rejected the plans because they were not elaborate enough". It sounds more like kicking the can down the road to me ... but ... whatever ...
In around a month I guess we'll know which Disney rumor-monger has the best information ...