I already gave my opinion on that. He starts there because THAT is where he fails, i.e. does not "stand and be true." He appears in the place shortly before the coach station wherein he met Jake. It is his sacrifice of Jake that damns him (in my opinion), assuring that his quest will continue even when he reaches the Tower. The top of the Tower is thus denied.
I cannot comment, because I do not think there is enough evidence one way or the other, on whether or not Roland's failure means the failure of the Tower. I tend to think Gan has many defenders and tools throughout the countless worlds. The Gunslinger is certainly one of the more important ones, but his failure (death prior to reaching the Tower) would not end all reality. If that idea were true we would have to assume the following:
1. The Gunslinger is Gan himself, an unknowing avatar set on the course of Ka and beyond it at the same time.
2. The Gunslinger is the Tower, i.e. a direct tool of Gan.
Neither of the above sound right to me. Roland is a man of destiny. He is a flawed protagonist of great importance, but some day the world will move on from him as well. If he were truly immortal, and unable to fail his suffering and/or victories and failures are meaningless. That would make Gan cruel and I simply don't see that.
Roland can fail in his quest or it isn't truly a quest. The problem is that Roland (and most people reading the book) see it as a quest for the Dark Tower. That is missing the forest for the trees. The horn is granted to Roland as a promise from Gan (or the Prim if you like) that things can be different. One does not make a liar out of Gan/God. This means I do not see the horn as some sort of important talisman or requirement to solve his quest so much as a token to ease a burdened soul being sent to the back of the line with the understanding, "you aren't ready yet but you are not damned and you might be ready one day."





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