#1. Why it's a bad idea: Undertaker matches haven't been exciting in years

This is the harsh reality of The Undertaker's current WWE career that people have been saying for years. When was the last great Undertaker match that you remember seeing? Perhaps the last good match he had was in 2015 against Brock Lesnar inside Hell in a Cell, but since then, it's all been downhill.
We can give multiple examples to prove it. Last year, his Super ShowDown match against Triple H was painful to watch. The Goldberg match at Super ShowDown this year was painful to watch. His alleged "retirement" match against Roman Reigns two years ago was painful to watch.
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As much as we love and respect The Undertaker for all that he's done for the business, the reality of it is that his matches contain no excitement and all the attraction in it is only due to the nostalgia factor.