I dunno, this looks like it's relatively easily resolved, to me. The confusion is that there are three possible outcome-states, not two. If you go on the roller coaster, you may or may not receive an update that lets you appreciate roller coaster rides. If you do receive it, it'll allow you to enjoy that ride and all future ones, but there's no guarantee that you will.

One possible ordering of those three outcomes is: go on TBMRR and receive update > go on teacups > go on TBMRR but don't receive update

Your most logical course of action would depend on how much you valued that update, and how likely it was that riding TBMRR would provide it.