#2 Undertaker and Shawn Michaels health
Time to be honest again.
Undertaker and Shawn Michaels aren't young men anymore and they are going to get seriously hurt if something happens inside the ring during this feud. Add to that the laundry list of injuries that The Undertaker and Shawn Michael's have suffered throughout their career and you'll realize that WWE is playing a very dangerous game.
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Sure, it's nostalgic! It's something that WWE hasn't done in a while and blurs the lines between fiction and reality, but it can't be backed up in the ring. Furthermore, any attempt to try to back up this storyline in the ring is most likely going to result in getting gassed, botching moves and injuring themselves, which could have very severe consequences.