You're right, he's been badly advised. But when he did his first transfer request, it'd be difficult to argue that United were 'no longer about trophies'.
I disagree. I think Rooney had become disillusioned by a series of events over a few years. I could be completely wrong - it wouldn't be the first time - but here's my take on it:
The quality of the side has been steadily diluted ever since the transfer of Ronaldo in 2009. That transfer was always going to happen, but what we should have done is immediately invest in 2-3 top drawer signings, both to make a statement and more importantly to keep the squad of a high standard. But we didn't. We also let Tevez go and our response to losing top 2 world class players was to sign Antonio Valencia, Gabriel Obertan and Michael Owen. That was the first biggest indication that our strategy going forward would be to give the illusion of being able to compete for trophies, whilst cutting player expenditure as much as possible. We didn't win the league that year, but only Chelsea were really any good anyway.
The following summer we brought in Smalling and Chicharito. Decent prospects, but still no sign of bringing in proven talent to not only 'replace' Tevez and Ronaldo, but to keep us at the cutting edge. We won the league in 10/11, but that papered over cracks. Arsenal had been imploding for a couple of years, City's splurge had yet to yield any consistency or effective approach and Chelsea continued to dick about. We had no real challenger and won the league by default.
Summer of 11/12, we signed De Gea. No argument there, but we HAD to sign a keeper as Van der Sar had retired. We signed Phil Jones - fair enough, but then pissed on our chips by signing Ashley Young and re-signing Scholesy (fuck me, of ever there was proof of what our signing policy had become). Still not enough talent being brought in considering the aging of Giggs, Scholes, Rio, Evra, Vidiv etc, the illness problems with Fletcher and the inability of Anderson or Nani to fulfill their potential.
City win the league and Fergie's response is to blame a sub-standard goal difference rather than look at the glaring deficiencies in the squad that caused us to drop points and piss away what should have been an unassailable lead. And aside from City, the rest of the least continued to be poor in relation to previous years.
Over the last 2 years, Chelsea have improved, so have City, Spurs and Liverpool. Arsenal have been reinvigorated by Ozil, and even teams like Southampton and Everton are improving. We've barely stood still, in fact we've gone backwards. And what we're seeing on the pitch is the consequence.
Against this backdrop, Rooney has been asked to play out of position in order to fill gaps that shouldn't be there. He's seen the team around him turn from top drawer to mediocre and he's become fucked off.
I think the persona of him being a money-hungry gobshite suits the clubs agenda. I genuinely don't believe that his motivating factor when he asked to get away in 2010 was money. I think he saw what was happening, called it out and was then rounded on by the club and given a wedge to re-sign, probably with some promises about new signings in the pipeline. The fact that he was then cast as a money grabber worked for the club - because it was better than the alternative of him gaining support for the idea that the quality of the side was becoming an afterthought. I think the way in which he was cast afterward pissed Rooney off, added to a lack of talent being added to the side and the way in which he was moved all around the side added to perhaps a grievance against comments made by Fergie to the press has led to where we are now.