Can Advertising in Windows Client Software Work?

MSN Messenger does it. Quicken does it. There’s a fair amount of Windows client software that has advertising – the same kind of banner ads present on most Web sites. But there are challenges to ad-powered client software, ranging from technical (how do you create an offline ad store) to sociological (will people be willing to live with ads in their local software).

I think that the technical issues, while non-trivial, are very solvable. What's more interesting is the idea of client software that's supported with advertising and how far our industry can take that before somebody cries foul.

There's certainly proof that people are OK with advertising in their applications -- just look at every ad engine out there. What's more interesting to me is how something like this could help small software creators make a revenue stream. By now we've all heard about Plenty Of Fish, the Canadian dating site where the creator makes $10K/day off of ads. But could the same work for my asphalt mix application creator?

Can people live with ads on their client? What are the blockers? What technial issues do you think the industry will run into? What sociological issues?