We need to find ways to make people upgrade

Isn't that a diametrically opposite paradigm to "Free as in Speech" ? Thats some scary stuff right there.

The large issue is that no software supplier in the world has successfully forced it's users to continually upgrade to the latest version as and when it want it to. We've 25+ years of data to support this in software, and about 1000 years to support it in Tech.

* Telling people to upgrade doesn't work.
* Making it easy to upgrade doesn't work.
* Making it cost effective to upgrade doesn't work.
* Making it more secure to upgrade doesn't work.
* Attempting to make people upgrade doesn't work.

To get people to upgrade anything, and I mean from a spork to WordPress to IE to their phone to their car - we have to make it a positive Return on Investment for them.

Right now we're not doing that, because we don't consider:
1) Time it takes to upgrade
2) Time it takes to test after WP has been released (can't do it in beta anymore, thanks Capital_P_Dangit)
3) Time it takes to programatically change all of the "decisions not options"
4) Time it takes to update the training material
5) Time it takes to train staff on whatever UI changes have been made this release
6) Time it takes to upgrade dependancies (plugins, themes, applications etc)

We shouldn't be making people do anything. If people aren't upgrading, we should find out why, so we can manage that better. But we're not.

As an aside: As of Monday our offices, and our clients, enter a 2 month code freeze. Its normal for us over the Christmas and New Year period to make sure we don't release any non-critical code that we'd end up having to support at the worst possible moment. WordPress 3.4 is scheduled for release the first week in March, just 4 weeks after our Code Freeze is lifted. As a company, a WordPress orientated company, we have no reason to upgrade any of our clients to 3.3, only to have to upgrade them to 3.4 just 4 weeks later. If only there was a Project Manager on the core team, but then the project manager would probably want at least 1 tester, and we don't want that now would we.

P.S. Hope your surgery went ok dude! I'm wishing you a speedy recovery.