Josh Porter effectively summarizes the conflicting points of view about the trade-offs between simplicity and feature-richness in Simplicity: The Ultimate Sophistication . Then he tries (pretty effectively I think) to argue that “We want simple decisions [in this case simple purchase decisions] as much as simple products.” Packaging and UI that communicates whether it will meet user needs is just as important as ease-of-use. Relates to my earlier quandary about choosing between Remember the Milk and Ta-da List ; apparently I’m not alone in hating to make those trade-offs. (By the way… I ended up going back to Ta-da after all; ease of sharing won out over mobility.)