Has a MITB contract holder ever
 

cashed in on someone, only for that person to purposely get disqualified or counted out to keep the title? If not, I feel like it would be good heel heat.

Honsestly, besides Cena being the "first ever to lose", and the deal with Ken Kennedy, there hasn't really been any other "creative shennanigans" to involve the case and cashing it in.

There are plenty of interesting avenues they can go down like the one in your question, but none of them have been explored as of yet (like the still potential swerve by Cody Rhodes, where Sandow cashes in, and Cody still has the OTHER contract from the original case and cashes in on him- effectively "stealing back" from Sandow for the MITB betrayal), but likely, they'll just treat it as business as usual, and Damien will cash in on whatever face wins it from Of The River.

Dunno, I feel like that crosses the line from good heel heat into cheap and shitty.

Has a MITB contract holder ever
 

beaten and then sexually assaulted a homless-man?

you photocopy the contract.

commission a few replica briefcases.

heel moves

I'm waiting for Sandow to cash in, lose, and then claim the contract wasnt in there since refs don't check, therefore giving him another shot.

also good ideas. I just think the idea of MITB is good but the statistics of it are pretty cheesy. Go some creative routes with it

Tried that in WWE Universe mode in one of the games. It was pretty stupid even in a video game.