The Washington Post published a series of articles about the market for individually-purchased health insurance and how it works for the 18 million Americans who buy it. The articles offer how-to guidance, even suggesting an HSA-compatible high-deductible policy.
One article reports that people leaving a workplace group-insurance plan have some options that others in the individual market do not. "First, under COBRA, which applies to workers at companies with 20 or more employees, you have the right to continue on your employer's plan for up to 18 months, and in some cases longer. Continuing in a group plan, which you do under COBRA, also makes you 'HIPAA-eligible' when you enter the individual market. HIPAA requires states to have at least two policies available without pre-existing condition exclusions. If a state doesn't have those two policies available, then it must set up an assigned risk pool."