Почему python-pip хранится в Ubuntu 14.04?

В вашем случае запустите

sudo apt-get dist-upgrade

вместо

sudo apt-get upgrade

Чтобы увидеть различия, прочитайте man-страницу: [!d3 ]

man apt-get

upgrade

Used to install the newest versions of all packages currently installed on the system from the sources enumerated in /etc/apt/sources.list(5). Packages currently installed with new versions available are retrieved and upgraded; under no circumstances are currently installed packages removed, nor are packages that are not already installed retrieved and installed. New versions of currently installed packages that cannot be upgraded without changing the install status of another package will be left at their current version. An update must be performed first so that apt-get knows that new versions of packages are available.

dist-upgrade

In addition to performing the function of upgrade, this option also intelligently handles changing dependencies with new versions of packages; apt-get has a "smart" conflict resolution system, and it will attempt to upgrade the most important packages at the expense of less important ones, if necessary.
The /etc/apt/sources.list(5) file contains a list of locations from which to retrieve desired package files. See also apt_preferences(5) for a mechanism for over-riding the general settings for individual packages.