This whole thing is dependent on how much Triple H wants to wrestle. Does he want to be a yearly attraction at WrestleMania or is he willing to get in the ring at the pay-per views each month? If it's the latter, then I see this playing out quite well over the next several months. There are enough legitimate main event players here (Trips, Orton, Batista, Kane, Bryan) to keep the entire program fresh....
I can see the quartet of villainous stars taking their turn at Bryan's title, which means we wouldn't be subjected to monthly rematches! Additionally, I can see ppv events that feature 8-man elimination matches in the main event, which is another way to keep the title scene fresh... Here's how I'd break down the program over the next several months:
Extreme Rules - Bryan vs. Triple H; Reigns vs Kane; Ambrose/Rollins vs Batista/Orton
Payback - Bryan/Shield vs Trips/Kane/Batista/Orton (Batista wins)
Money in the Bank - Bryan vs Batista; Orton vs Ambrose; Reigns, Kane, Rollins in MITB (Reigns wins)
Battleground - Bryan vs Orton; Batista vs Reigns; Orton vs Ambrose
SummerSlam - Bryan vs Orton vs Batista - Bryan wins. Reigns cashes in.
This isn't perfect, and it could use some tweaking, but what I like about this is that the title match is different every month - even going so far as not to have a title match at all in June. Additionally, if Reigns is acting as Bryan's friend, then his winning the MITB adds a layer of distrust, which eventually gets paid off in Reigns' heel turn at SummerSlam.