I actually see the need for change driven by the move towards 64 bit systems rather than a Windoze deadline. In the next decade we will probably be quite nostalgic about 32 bit systems as we are today about 8 and 16 bit systems.
A good business would deal with the upgrade issue as follows: All infrastructure needs to be life cycle managed including IT infrastructure. Either one pays small amounts in upkeep as they chug along or pays one large amount up front for a clean slate every 5 years or so - if done properly the costs should even out over the life cycle of the infrastructure.
For us personal users the IT budget is significantly smaller and writing off assets that are still working becomes difficult without a tax offset. I have a pressing need for 64 bit computing but I cannot see myself updating my standalone XP computer (not my XP laptop) which has thousands of dollars worth of software on it that all works very well.
I guess there will be many millions of users stuck in that same predicament for some time to come.