1) Should he announce when he's cashing it in? (He'll be the third man to do this, behind RVD and Cena)

2) Should he be the second man to cash it in during a championship match? (Behind Rollins)

3) Should he lose during his cash in? (Third man, behind Cena and Sandow)

4) Should the MITB briefcase be put on the line again every so often? (Last time this was done was in 2012 with Ziggler)

Basic after-match cash in IMO.

It should actually be at Summerslam where Cena wins & Sheamus cashes in. Unless that's too obvious or WWE isn't ready for that at this time.

^
No way Cena will equal Flair's record just to lose it 2 minutes later lol.

TBH, I'm not sure what I would do...or what they'll do. I don't really want Sheamus as World Champion right now :\

Oh yeah I forgot Cena is about to tie that. I thought he was still 2-3 reigns off.

I could see it being a failed cash in

This is what's going down, imo.

R-Truth will start carrying around a lunch box and calling himself "Senor Cash in the Wallet" and he'll go on to tell everyone about how he's going to become the next world champ. Sheamus will get mega pissed because he hasn't got a sense of humour and he'll challenge R-Truth to a lunch box vs briefcase match and the winner will become the first ever "Senor Cash in the Bank". R-Truth will win that match with a schoolboy after an accidental distraction from Becky Lynch, who will be Sheamus' valet at that point because she's Irish and the company will be fed up of the whole divas revolution thing.

Then R-Truth will turn up at an NXT Takeover event and will try to cash in on Finn Balor after he's had a gruelling main event with Enzo Amore. The referee will point out that he can't cash in for the NXT championship and then R-Truth will apologise to everyone and leave. After that he will be the first person to completely forget to cash in for the World Championship before the contract expires and go down in the history books and become forever immortal.

Book it.

^