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I'm wondering if this is possible or if there is some schedule conflict between some side quests.

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your edit is a different question, so please ask a new question –  Zommuter Jun 2 '11 at 19:10
    
Hm, I propose asking a new question as in "How many three days periods are required at minimum to obtain all masks?" –  Zommuter Aug 29 '12 at 20:11
    
@Zommuter Ask away in a new question! :) –  CyberSkull Aug 30 '12 at 0:40
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4 Answers

up vote 9 down vote accepted

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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Then do you thinkl anything would prevent me from gathering all the masks except Deku/Goron/Zora in a 3 days period? –  pwny Jun 2 '11 at 16:10
    
@pwny Unlikely, to get the Romani's Mask you'll have to spend too much time at the farm to obtain the others. Although it may be possible, especially you slow down time with the ocarina. –  Zommuter Aug 29 '12 at 20:06
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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:

Remember that letter that the Curiosity Shop man gave to you? Well, it needs to be delivered to Madame Aroma. You can either hand deliver the letter to Aroma (you’ll need the Romani Mask for this), or you can hand the letter to the frantic postman at the post office. If you choose to deliver the letter to Aroma yourself, [...] she’ll reward you with a new bottle that’s full of Chateau Romani. If you take the other route and give the letter to the postman, [...] talk to him to receive the postman’s hat.

There are a few other sources stating the same thing.

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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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That's the most important example indeed. Also one has to spent much time at the farm to obtain Romani's Mask, so it's likely impossible to do it in only two three day periods –  Zommuter Aug 29 '12 at 20:10
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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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Is that counting the Temples themselves as sidequests? –  Wallace Brown Nov 26 '12 at 18:08
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