In respect of journalists, my take is this:
Lee Ryder only gets information he's "allowed" to have. When Ashley/Barnes decides it's ok to release snippets like "tyre kickers" or "remain sceptical", that's when Ryder hears about it. He remains a media outlet for the club - he had a falling out with NUFC about ten years ago or so and the Chron were admonished by Ashley for their reporting. They had to peel it back quite a bit and now only Douglas puts his name to the more anti-Ashley headlines. So when Ryder says something, it's coming from sources Ashley allows, hence why it's always tentative/negative.
Caulkin, Waugh et al, openly despise Ashley and have never sought access to SJP because they are only too aware that it's of no interest. Banal soundbytes from Bruce mean nothing, so they choose to seek information elsewhere and report it based on standard journalism efforts. So their information on the takeover is sourced from within the PL, within Staveley's camp, and so on.
The issue, of course, is Ashley. He's never going to say anything, nor will he allow his mouthpiece Ryder to publish anything revealing or optimistic. Similarly, I'd imagine Staveley is being told one thing by Ashley but he's quite capable of acting differently. So the bottom line is Ryder is likely the least reliable source of tidbits but if things become official may well be the one to break the news. The rest are almost certainly on the right lines, but are always open to Ashley doing something stupid/random and the whole thing falling apart. At which point nobody will comment, except Ryder who will publish something like "Ashley said along he was sceptical and so the outcome is as expected".