Same problem here. Since I upgraded to Trusty Tahr syslog stopped rotating.
$ /var/log# ls -la syslog*
-rw-r----- 1 syslog adm 35897990 Sep 24 14:10 syslog
-rw-r----- 1 syslog adm  3083621 Aug 19 06:36 syslog.1
-rw-r----- 1 syslog adm    37647 Aug 18 06:43 syslog.2.gz
-rw-r----- 1 syslog adm    40009 Aug 17 06:42 syslog.3.gz
-rw-r----- 1 syslog adm    60140 Aug 16 06:39 syslog.4.gz
-rw-r----- 1 syslog adm    63035 Aug 15 06:38 syslog.5.gz
-rw-r----- 1 syslog adm    59387 Aug 14 06:40 syslog.6.gz
-rw-r----- 1 syslog adm    66224 Aug 13 06:30 syslog.7.gz

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You received this bug notification because you are a member of Ubuntu
Touch seeded packages, which is subscribed to logrotate in Ubuntu.
https://bugs.launchpad.net/bugs/1278193

Title:
  logrotate skip the rotation of many files under /var/log due to bad
  group ownership

Status in “logrotate” package in Ubuntu:
  Confirmed

Bug description:
  With the latest update to logrotate (3.8.7-1ubuntu1), the group
  ownership of /var/log was changed to "syslog" causing this kind of
  problem:

    # logrotate -df /etc/logrotate.d/rsyslog
    reading config file /etc/logrotate.d/rsyslog

    Handling 2 logs

    rotating pattern: /var/log/syslog
     forced from command line (7 rotations)
    empty log files are not rotated, old logs are removed
    considering log /var/log/syslog
    error: skipping "/var/log/syslog" because parent directory has insecure 
permissions (It's world writable or writable by group which
    is not "root") Set "su" directive in config file to tell logrotate which 
user/group should be used for rotation.
    ...

  
    # ls -la /var/ | grep log
    drwxrwxr-x 17 root syslog   4096 Feb  9 10:58 log

  $ lsb_release -rd
  Description:  Ubuntu Trusty Tahr (development branch)
  Release:      14.04
  $ apt-cache policy logrotate
  logrotate:
    Installed: 3.8.7-1ubuntu1
    Candidate: 3.8.7-1ubuntu1
    Version table:
   *** 3.8.7-1ubuntu1 0
          500 http://archive.ubuntu.com/ubuntu/ trusty/main amd64 Packages
          100 /var/lib/dpkg/status

  ProblemType: Bug
  DistroRelease: Ubuntu 14.04
  Package: logrotate 3.8.7-1ubuntu1
  ProcVersionSignature: Ubuntu 3.13.0-8.27-generic 3.13.2
  Uname: Linux 3.13.0-8-generic x86_64
  ApportVersion: 2.13.2-0ubuntu2
  Architecture: amd64
  CurrentDesktop: Unity
  Date: Sun Feb  9 17:19:41 2014
  InstallationDate: Installed on 2014-01-26 (14 days ago)
  InstallationMedia: Ubuntu 14.04 LTS "Trusty Tahr" - Alpha amd64 (20140124)
  SourcePackage: logrotate
  UpgradeStatus: No upgrade log present (probably fresh install)

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