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HealthSherpa is easier to use and looks cleaner, but I don’t find healthcare.gov too messy. The official site has more features, so the extra menus and buttons are understandable.
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It is worth noting that healthsherpa.com uses Bootstrap (essentially, a collection of components that can make web design easier) and very nothing else on the front end, thus any appreciation for healthsherpa’s design should go to Bootstrap.
However, having previously designed for public sector companies, I believe healthsherpa’s emphasis on what people really want (i.e. “what’s my plan” rather than “Here’s a FAQ full of things we wish people would ask”) is commendable.