I'll indulge you, and try to answer all of the questions you posted directly.
It's difficult to claim that DiBiase is still at a championship level when he's never actually won a title save for his tag titles which were a good couple of years and then some ago. Since that time, despite WWE trying to push him, it's been a story similar to that of Del Rio. You can see WWE putting plenty of stock in him, but his runs have done nothing because he just isn't that good a talent.
It's strange how genetics works. You can have someone like Ted DiBiase senior, a very talented and memorable performer, produce a kid and have them be nothing but an average wrestler. Conversely you can take Dusty Rhodes and he'll engineer a man with all the potential in the world. Ted DiBiase, for all the stock they put in him, and time they want to give him on TV is, unfortunately, just another average talent. DiBiase probably ISN'T at a championship level. He doesn't compete for the US or IC titles apart from that one short run with Rhodes, which flopped when people didn't buy him as a face. They even made light of how far from grace he'd fallen when he was resigned to being Rhodes' lackey for that period last year.
Whether he goes to Raw or Smackdown matters very little. As you probably know, Raw is a supershow and talent from Raw or Smackdown can be featured on it. If he's good enough, or promising enough (such as Ryback) he'll be featured on both shows. Regardless, whatever show you are officially signed to doesn't have to dictate which champion to try to cash in upon so I see it of little consequence which show he lands on. It's nothing but a name.
When he returns, I expect that he will, at least for the time being, be relegated to performing on Superstars and having the occasional match on either of the main shows but nothing of consequence. Whether things go north for him from there, I have my severe doubts.
In the end, I'm afraid I don't see DiBiase as a talent likely to win MITB at this stage. It'd equate to Tyson Kidd or Yoshi Tatsu winning it, which I think you can agree would be head-scratching. Even regardless of my feelings on him, he just doesn't have enough momentum to be able to justify WWE rewarding him in this way. If you're talking potential MITB winners (bear in mind we can all be thrown, few people expected Daniel Bryan winning last year) we are probably talking at names from this list; Cody Rhodes, Wade Barrett (if he's back in time), Ziggler, Del Rio, Jericho, Miz or for faces; Mysterio, Kane (not sure where to put him), Ryder, Alex Riley, Mason Ryan. I'm really reaching with some of those but you get the point. DiBiase is probably not on that not so highly exclusive list.
I wouldn't bank on it.
