One of the biggest downsides of paying for your own plan is that your premiums might not be pre-tax as they would be if you were paying for a plan that your employer and your contribution towards the plan was being taken off your paycheck. But, if you own your own business, you can potentially write off those expenses as a business cost and therefore get the same savings.
Often, there is no waiting period in a group plan, like one offered by an employer. Of course, if you were eligible for a company-based plan, you probably wouldn't be shopping around on your own. However, the same privilege might be had in a group plan offered through an organization such as AARP.  With their plans, there's no waiting period for preventative services, at least.   
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