Questions for Cleveland:
Vince Carter isn't, and really never has been, a small forward. Can he effectively play there in your lineup?
You have multiple quitters on your team, in Vince Carter and AK47. Where does the mental and physical toughness come from on your team?
Sadly, I am no longer Cleveland, though I hear my former Cavs are in good hands.
Carter at SF is a concern, but playing next to a huge SG in Joe Johnson helps mask some of his deficiencies. Mike Dunleavy's ability to play at SF also means that when JJ comes out of the lineup, VC can move to his more natural SG with Kirilenko or Dunleavy taking over at the 3. If my lineup wasn't so fluid, it would be a concern, but I am confident that VC can handle a role as a hybrid 2/3 as long as he's got a big mate in the backcourt.
As far as the culture of losing, VC and AK47 are sulkers with poor reputations, but they've been bolstered by guys with winning reputations, both young and old. Lawson and Aldrich have NCAA titles, JJ and Terry have been parts of long winning traditions recently, and even despite their problems, VC and AK are both fixtures in the playoffs.
Chemistry is a concern, but in a free-flowing offense with lots of touches to go around, I think they'll be able to find a common ground. Winning helps alleviate these problems, but so does scoring in bunches - and I think that will be a major benefit of playing for the fake Magic.
Plus, Josh McRoberts once helped free hostages from a North Korea prison camp, so if his communicative skills are needed to calm tensions, he'll be pressed into action.