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Well that is all true, but perhaps user 2 had no reason to upgrade, or perhaps he didn't like the versions between his current one and the latest.  There have been two releases of my current software that have frankly left me completely cold, and I wouldn't have upgraded my sites to them other than I have to as a resource provider.. but they were eventually replaced by excellent releases.

For my own site I have always paid the upgrade fee(s) for the multiple licenses and all the add ons I used to hold, however I had one personal site that really has languished due to lack of time/commitment to it, paying the $50 per year from my current provider would have been a complete waste of money, and I didn't draw on their resources at all during that period of time, as a multiple license holder paying a whole lot of annual fees when I rarely use support I have no moral dilemma with missing a year or so of one license, until an upgrade is warranted.

I like the idea of Encouragement being with Carrots rather than Sticks myself