MS Azure - 5 "Editions" and counting
One thing that MS doesn't get with its transition to the cloud is simplication. Windows is sold in too many "editions", Office is sold in more additions that there are products in the suite and now Azure continues the trend. There are already 4 additions available and a 5th coming in August (http://www.microsoft.com/windowsazure/offers/)
Compare that to Google Apps - free up to specific limits and then simple unit fees for usage. (http://code.google.com/appengine/business/#billing)
If the market really is small businesses, perhaps selling a service that doesn't involve a legal team to choose the correct edition would be a place to start.