[jaredsohn]

>It is hard to get everybody up to the latest version (even if the upgrades are free)

Automatic patching helps with this, although it requires a little more work designing a patching system (you might not want everyone hitting your servers at once), and it doesn't affect everyone (some people's computers are offline or require a proxy to be set up for patching.)

[jetti]

That is true, but even that has its caveats. Depending on who your target is, the user may be skeptical of a program "phoning home" on its own every so often.