ask them about their car and you'll hear something like "2005 Honda S2000" :-)
If Apple was updating the iPad multiple times per year then yeah, the year wouldn't be very useful.
As far as Microsoft, maybe they realized that using year for something that's not updated every year has a downfall - by 98 something called 95 sounds quite dated, especially in the computer industry. Of course they're still using that to some extent: Office 2010, Visual Studio 2010.