I'm wondering if this is possible or if there is some schedule conflict between some side quests.
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This is impossible. For a start, to win the lottery side-quest you have to go back in time at least once to know what the numbers are going to be/were. To get the lover's mask side-quest completed you need to return to the first day and show the lover's mask to the major to get a heart piece. |
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No. This walk through of the Kafei and Anju side-quest states it can be completed in two different ways, one of which gives a bottle, the other the postmans hat:
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To answer the original question and the edit at the same time: No, it is impossible. To get the All-Night mask at the Curiosity Shop, you must save the old lady in North Clock Town on the first night. This causes Sakon not to visit the Curiosity Shop, stopping the Kafei-Anju quest, meaning you cannot get the Keaton mask, or the Lover's mask. |
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The lottery isn't a sidequest, really, since ever doing it isn't logged anywhere. You need to do at least 2 cycles to fully complete all sidequests. However, it is possible to beat the game itself (ignoring all sidequests) in just one cycle (after the initial 3 days needed to get your Ocarina and human self back, of course). |
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