I wouldn't be surprised to see Cleverley go out on loan to a team like Newcastle/Bolton/whoever, being an important player for them, and then end up staying there permanently. A bit like Guthrie for Liverpool, went to Newcastle and then eventually stayed for games. I think the one thing he has in his locker that will be of great benefit in getting games here is his versatility, as it's always been an asset we've valued in the younger players and Sir Alex has even went to point that out. He's obviously quite talented too, but I don't think he'd be making this team on talent alone so his versatility will serve him well.
I just think that with Anderson already here and performing a similar role in the middle to what we'd expect of Cleverley, and then us having a reasonably well stocked wingers group, I think he'll have a tough time of breaking into it and have to show a commendable level of patience - but if he does have that kind of character, then he'll have a good chance of a very good career with us I think. I know that the most important factor above all in a young player breaking through is timing, and taking that into consideration you look at the players that he might be coming in to replace in the near future:
Park - Very similar in style, and if Cleverly was willing to be as loyal and play a similar role in the team then maybe there's a place in the squad for him there...but he's only just signed a contract extension to keep him at the club until 2012, and seems happy at the club so I can't see us selling him, so it'll require a lot of patience from Cleverley. If he is willing to wait that long then he'll be a great asset, and I'll be proved wrong to a huge degree.
Giggs - Plays either a slightly withdrawn wing-role, or as a dribbling, creative playmaker through the middle, there's again a lot of similarities you can draw between the two players and it does show there's a role in the team for him. Again though, you can see Giggsy going on for two years so it'll require patience, and then you ask the question about whether Giggsy's positional successor is already in the squad in Nani and so that leaves Cleverley back on the bench a lot of the time to compete with Obertan.
The way I see it is in two years we'll probably have lost Giggsy, Scholesy, Park(31 - back to Asia?) and Hargreaves from the midfield. That'll leave us with a midfield of Carrick, Fletcher, Anderson and possibly Gibson from the current team, so there is a space or two for Cleverley, but whether he'll be able to convince enough to stop the (new?) manager from instead buying a new top-level midfielder in the team from now until then is where I'm unsure and not all that confident about.
Obviously this is looking too far into the future, and is very presumptuous about his character and the managerial decisions (to start with), and I don't expect(or even want) many to agree with this...but I'll be very surprised to see Cleverley make it. He's good, you could argue better than Gibson even, but I think that he's got less of a chance of making it due to the balance of the squad roles and his own ambition to be a big part of a team, which he's certainly good enough to do at another good team.