Yup, but with a roster this overloaded, who would we have gotten for 25% of the mid-level? That's less than 2 million per year ... Actually his contract isn't quite the obstacle you're making it out to be. He's only going to be making about 6 million per year (even with raises) every year after this; given the nature of the CBA and the way that trades have to match up in terms of salary he probably makes it easier to move (somewhat paradoxically). If all he does is shoot a high percentage, play credible wing defense and hustle he'll add value to the team ... probably not enough to fully justify the pricetag, but we're not talking about an over-the-hill full MLE guy like James Posey entering his decline.
Huh? When did he say this? All I remember is his interview when he was in Vegas and he made it a point to say that he was working on his off-the-ball game, not that he needed to play point guard or handle the ball more than he already does.
You can divide up the MLE among more than one player, as I recall. Basketball Prospectus did a study last year and found that full MLE contracts tend to be the worst free agent values. Players signed to full MLE contracts rarely are anywhere close to worth it. That said, even if I think that Matthews is likely to continue that trend, I still think it is worth the risk if Allen is willing to pay the freight (without skimping on re-signing players like Oden and Batum). As you said, and I've noted before, once you're over the cap, you're over the cap. It doesn't really have any significance to team-building whether you're over by $1 or $100 million as long as the owner can afford it, with luxury tax. On the small chance that Matthews turns out to be a good player, it's worth going for.
In the interview he said he was going to work on his off the ball game as well as improving with the ball in his hands. He never stated he is going to be playing Point Guard, however he mentioned he will talk to Nate about lineups with Batum and Matthews on the floor together. Hence, the assumption Roy could be playing PG with those two on the floor at times.
That sounds like an end-of-game kind of scenario ... which I think is probably a good idea, especially given Batum and Matthews catch and shoot ability on the wing.
Yes or at points during the game when you need a defensive unit on the floor. I think some got a little carried away and starting debating whether Roy should play 20+ minutes at the PG spot a game when in reality, he would play spot minutes to allow Matthews and Batum on the floor together at times.