Oregon's problems with the Cover Oregon site are reflective of a procurement process mired in the 1980s. Indeed, this is a problem at all levels of government, and is one of the issues to plague HealthCare.gov. The officials specing and evaluating proposals characteristically have little comprehension of modern software development, and simply give the contract to whatever proprietary vendor does the best marketing job on them.
Another recent, but unnoticed example of this skewed process, also from Oregon, is the awarding of the state's online portal development to a vendor clearly chosen, by key officials, before the process of selection even started. No consideration was given to open development or open standards, the meetings leading up to the purchase decision were just sales presentations by said vendor.
Truth is free, but information costs.