He is likely better than half the idiots running. That said, will he pull support from the establishment guys or from the outsiders?
For S&G's, I'll assume for a minute he is actually serious about running this time and isn't just media whoring. I'm not saying that's likely, mind you, just that I'll go with it for pure entertainment value.
I don't think he gives a crap about establishment folks, outsiders, talking heads, or pretty much any special interest groups. The man's got enough of his own money to fund a campaign that outspends the entire rest of the pack, likely several times over, without a dime from anyone being tossed at him. And to still get on with life afterwards if it doesn't work out.
Which means he doesn't need them. He know's it, they know it, and that's why he's being able to say unpopular and inflammatory things and make peoples heads explode. And frankly some of these things have been said for years by folks who have now become disenfranchised by beltway stupidity. Seriously, we aren't even far in to it and it's been fun to watch. All he needs to bank on (again, devils advocate I'll assume for a minute he's serious) is if he says the right unPC things he'll engage people, wake up the majority of folks who feel the same way but generally sit on their ass, even the ones who may not agree with him 100% like him being brutally honest and screwing the political class, and get them to the polls. Which is pretty much what he's said his strategy is.
Will it work, if he takes it long term? Who knows. But it'll be freakin entertaining.