alexonfyre

Let's rephrase the question, as you are, to say "Getting to Super Bowl" "Having gotten to a super bowl, win it" or "Having won a super bowl, winning again within 3 years"

The probability of winning one game is almost always going to be higher than the probability of winning the number of games necessary to get to that game, so generally, as you said, getting to a super bowl is harder than winning one, even when getting to that super bowl was relatively easy.

However my answer doesn't change

The last task still implicitly contains both getting to and winning a super bowl in a different season, and the combination of those tasks will always be more difficult than either one individually. Further, to say that in some instances the second super bowl run could be easier than the first, and therefore that task is easier to accomplish is a fallacy of converse accident. Even if you only posit that hypothetical to say that it makes the answer "not obvious" then you make the question trivial, because you can then say that about every element, and there is no credible way to defend any of them. Finally, if you want to go the route of facts, then:

28 teams have gotten to a Super Bowl
18 teams have won a Super Bowl
7 teams have repeated within 3 years

There is simply no angle that you can approach this question from and not come to the conclusion that repeating is clearly the hardest challenge.