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Let's say Ubuntu's repositories features a package.

I install that package using apt-get.

I then add an additional source (with add-apt-repository) that lists either a newer or older version of the package.

Will apt-get always upgrade to the latest version, regardless of which source offers the latest version?

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up vote 6 down vote accepted

APT will always install the latest version that isn't excluded by preferences. Preferences are indicated in the file /etc/apt/preferences (and in files under /etc/apt/preferences.d).

Some repositories have a configuration that prevents their packages from being installed automatically. For example, the Debian backports have release files (which you can see in /var/lib/apt/lists) that contain

NotAutomatic: yes
ButAutomaticUpgrades: yes

If you have multiple sources for the exact same package (i.e. same package name, same version number), then APT downloads from the first source found in /etc/apt/sources.list (or /etc/apt/sources.list.d/*). So list local mirrors first. The order in sources.list is irrelevant for packages that have a different version number.

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