Whom should I ask for upgrading the particular package, if there is a new upstream release?
Should I file a bug report?
What if the package is maintained by Debian maintainers? Should I leave a comment at their mailing list?
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3See What can I do if Synaptic can't get the latest version of software? and Why can't I update applications without upgrading the whole OS? to understand the policy relating to updating software. – Jan 06 '13 at 17:57
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The maintainer of the package. He might already be working on it!
How? Doesn't really matter. I see bug reports for it, but usually this is discussed behind the scenes. I guess most is being discussed using IRC and mailing lists. Depends on the package and the people working on it.
Debian/Ubuntu developers (package maintainers) are uploading new releases to experimental/unstable and will end up later in a stable channel via regular QA process. A new upstream release isn't usually going to be included in a stable release. Security or severe bugs come as regular updates, without backporting a whole new release.
Exception: web browsers.
See also this answer on the policy regarding updates within Ubuntu.
