Roland deserved some kind of consolidation for everything he went through, not to just go through it all over again.
But each time Roland makes his journey he does get consolidation. On his next journey he will have the Horn Of Eld with him and that will make his journey better/easier. Maybe with the Horn with him this time it will be his last. It's up to you to decide if/when Roland finally is at peace with himself and his journey. That is what makes the ending so wonderful- you, not King, are the author of Roland's journey.
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