It's definitely tough and you're right, it's also easy to make feature-based segmentation infuriating. But (as you know and as this thread amply demonstrates) for pro-sumerish apps, it's as much (if not more) about vibes as it is about price. The 'we're simple software artisans asking an honest price for a quality product' vibe just clashes with the nickel-and-dime vibe of that pricing structure, that's all.