I would say he has the sensible attitude. People (largey) didn't want to upgrade to Vista. XP does what people need it to on the hardware they use - and Microsoft and developers will support XP for ages to come.
Why should you upgrade just because Apple (and, as it happens, OS X developers) practically force you to? Apple has always been a "we do things our way, you either come with us or you don't" company; just look at Steve Jobs' stance on Blu-Ray! They certainly aren't pushing forward with optical discs are they (my theory: to peddle the iTunes Store...)?
Apple don't make a better product, they make an alternative product that is better in some areas, worse in others. And it doesn't stand on its own merits, Apple release adverts that bend the truth all kinds of places about Windows just to make them look better.
Yes, you have to make a trade off between supporting older systems and pushing further with newer ones. The problem I have is "pushing" us onto Leopard SP1 and charging $129.00/£83.00 for the privilege.