Does iTunes upload music on weekends?

Hi. I was wondering if iTunes uploads music on the weekends. There is a new epic rap battles of history coming out, and it is always on iTunes early.

This isn't an issue of putting songs on that I don't want, it's that it doesn't CHANGE my music, even when I try to make it change.  I've got over 15000 songs in my iTunes; my iPod can only hold around 275 songs.  My problem, is that I can't make it "randomly" choose different songs.  when I try to change the music, it puts the same songs on over and over.
Emphasis here is on RANDOM: I do not want to have to select the music to put on my shuffle. and
CHANGE: If I only wanted to listen to the same 275 songs, I wouldn't have bothered purchasing the others...

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    M:\Music\Media\Music\Phil Collins\Hits\07 Against All Odds.mp3
    StartTag                   : TagLib.NonContainer.StartTag
    EndTag                     : TagLib.NonContainer.EndTag
    TagTypes                   : Id3v1, Id3v2
    Tags                       : {, }
    Title                      : Against All Odds
    Performers                 : {Phil Collins}
    PerformersSort             : {}
    AlbumArtistsSort           : {}
    AlbumArtists               : {Phil Collins}
    Composers                  : {Phil Collins}
    ComposersSort              : {}
    TitleSort                  :
    AlbumSort                  :
    Album                      : Hits
    Comment                    :
    Genres                     : {Adult Contemporary}
    Year                       : 1984
    Track                      : 7
    TrackCount                 : 0
    Disc                       : 1
    DiscCount                  : 1
    Lyrics                     :
    Grouping                   :
    BeatsPerMinute             : 121
    Conductor                  :
    Copyright                  :
    MusicBrainzArtistId        :
    MusicBrainzReleaseId       :
    MusicBrainzReleaseArtistId :
    MusicBrainzTrackId         :
    MusicBrainzDiscId          :
    MusicIpId                  :
    AmazonId                   :
    MusicBrainzReleaseStatus   :
    MusicBrainzReleaseType     :
    MusicBrainzReleaseCountry  :
    Pictures                   : {}
    IsEmpty                    : False
    Artists                    : {Phil Collins}
    FirstArtist                : Phil Collins
    FirstAlbumArtist           : Phil Collins
    FirstAlbumArtistSort       :
    FirstPerformer             : Phil Collins
    FirstPerformerSort         :
    FirstComposerSort          :
    FirstComposer              : Phil Collins
    FirstGenre                 : Adult Contemporary
    JoinedArtists              : Phil Collins
    JoinedAlbumArtists         : Phil Collins
    JoinedPerformers           : Phil Collins
    JoinedPerformersSort       :
    JoinedComposers            : Phil Collins
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    File2:
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    StartTag                   : TagLib.NonContainer.StartTag
    EndTag                     : TagLib.NonContainer.EndTag
    TagTypes                   : Id3v1, Id3v2
    Tags                       : {, }
    Title                      : Ich Wäre Gern Wie Du
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    AlbumArtistsSort           : {}
    AlbumArtists               : {Disney}
    Composers                  : {R. M. Sherman}
    ComposersSort              : {}
    TitleSort                  :
    AlbumSort                  :
    Album                      : Das Dschungelbuch - Deutscher Original Film-Soundtrack
    Comment                    :
    Genres                     : {Film-musik}
    Year                       : 2007
    Track                      : 6
    TrackCount                 : 0
    Disc                       : 1
    DiscCount                  : 1
    Lyrics                     :
    Grouping                   :
    BeatsPerMinute             : 0
    Conductor                  :
    Copyright                  :
    MusicBrainzArtistId        :
    MusicBrainzReleaseId       :
    MusicBrainzReleaseArtistId :
    MusicBrainzTrackId         :
    MusicBrainzDiscId          :
    MusicIpId                  :
    AmazonId                   :
    MusicBrainzReleaseStatus   :
    MusicBrainzReleaseType     :
    MusicBrainzReleaseCountry  :
    Pictures                   : {}
    IsEmpty                    : False
    Artists                    : {Disney}
    FirstArtist                : Disney
    FirstAlbumArtist           : Disney
    FirstAlbumArtistSort       :
    FirstPerformer             : Disney
    FirstPerformerSort         :
    FirstComposerSort          :
    FirstComposer              : R. M. Sherman
    FirstGenre                 : Film-musik
    JoinedArtists              : Disney
    JoinedAlbumArtists         : Disney
    JoinedPerformers           : Disney
    JoinedPerformersSort       :
    JoinedComposers            : R. M. Sherman
    JoinedGenres               : Film-musik
    File3:
    M:\Music\Media\Music\Compilations\Album\9999 Title.mp3
    StartTag                   : TagLib.NonContainer.StartTag
    EndTag                     : TagLib.NonContainer.EndTag
    TagTypes                   : Id3v1, Id3v2
    Tags                       : {, }
    Title                      : Title
    Performers                 : {Contributing artists}
    PerformersSort             : {}
    AlbumArtistsSort           : {}
    AlbumArtists               : {Album artist}
    Composers                  : {Composers}
    ComposersSort              : {}
    TitleSort                  :
    AlbumSort                  :
    Album                      : Album
    Comment                    : Comments
    Genres                     : {Genre}
    Year                       : 2013
    Track                      : 9999
    TrackCount                 : 0
    Disc                       : 0
    DiscCount                  : 0
    Lyrics                     :
    Grouping                   : Group description
    BeatsPerMinute             : 1111
    Conductor                  : Conductors
    Copyright                  :
    MusicBrainzArtistId        :
    MusicBrainzReleaseId       :
    MusicBrainzReleaseArtistId :
    MusicBrainzTrackId         :
    MusicBrainzDiscId          :
    MusicIpId                  :
    AmazonId                   :
    MusicBrainzReleaseStatus   :
    MusicBrainzReleaseType     :
    MusicBrainzReleaseCountry  :
    Pictures                   : {}
    IsEmpty                    : False
    Artists                    : {Contributing artists}
    FirstArtist                : Contributing artists
    FirstAlbumArtist           : Album artist
    FirstAlbumArtistSort       :
    FirstPerformer             : Contributing artists
    FirstPerformerSort         :
    FirstComposerSort          :
    FirstComposer              : Composers
    FirstGenre                 : Genre
    JoinedArtists              : Contributing artists
    JoinedAlbumArtists         : Album artist
    JoinedPerformers           : Contributing artists
    JoinedPerformersSort       :
    JoinedComposers            : Composers
    JoinedGenres               : Genre
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