My experience is with enterprise software, where most products were born as shrinkwrap and slowly moved to other models, and I agree, it's not an easy problem to solve. Even if you size lifetime costs correctly (and very few people can), it is quite hard to scale a support org; even if one can see the storm coming, one might not be fast enough to be prepared for it for a number of reasons (geography, capital investment, training times, churn, brain drain, etc etc).

That's why some big names have literally declared support bankruptcy and just don't provide almost any support (google, amazon...).