Coverage Disruptions

I came across this story on NPR this morning that discusses the difficulty of navigating the insurance market for individuals that experience coverage disruptions. The article points out a few scenarios that may occur when a spouse retires, becomes eligible for Medicare, and loses private insurance. For example,

1) A spouse that retires and becomes eligible for Medicare risks their dependent spouse having to shop for health insurance in the individual market,
2) A dependent child (under age 26) may have to purchase expensive COBRA insurance when their parent retires and loses private insurance coverage (even though the ACA mandates their coverage on the private plan), or
3) An employee of a small employer (20 employees or less) decides to keep working and stay enrolled in the companies private plan even though they are eligible for Medicare, risking the private company recouping the costs provided to a technical Medicare beneficiary.

I think the article points out very complex scenarios that are not that rare. My main concern is the ability of the average person to shop for health insurance in a complex environment. How will Medicare and insurance companies provide transparency for enrollees facing these situations? Will this result in higher  premiums as companies increase administrative costs to meet patient demand (Thanks, Justin!)? Moreover, assuming vouchers become the Medicare reality, how will new Medicare enrollees and the elderly without a health care advocate make informed plan decisions? I think these are issues the current administration and potentially a new administration will have to answer prior to 2014.