The problem behind the problem for (2) is that upgrades can be DOWNgrades, too. And if your software depends on something that WILL disappear with the upgrade (like support for the ISA bus which was dropped with Vista), then you're up against the person who's sworn to stand his ground to the death, meaning no carrot is more valuable than where he stands right now and amount of stick will make him budge. The thing is that one size can't necessarily fit all and for some, there are higher priorities than anything you can provide.