I would suggest that the reason most people can't, or won't, upgrade their older versions is due to a reliance on 3rd party plugins that are incompatible with newer versions of wordpress.
Anytime I speak with a site owner having issues with their blogs, it seems to point back to themes using deprecated calls or a reliance on 3rd party plugins that are no longer actively developed.
When deciding to use plugins, it's a good idea to choose ones that will not completely break a site's functionality should you upgrade and have to disable it.
Personally, I would recommend using as few 3rd party plugins as is possible. For ourselves, a little scripting in the themes we use allows us to not rely on most plugins. (I think we use 2, maybe 3, none of which breaks functionality if an incompatibility exists (ex. Akismet)).
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