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I'm pretty lucky as far as health and dental insurance goes, my wife is retired from General Motors and we have the creame de la creame of insurance plans.
I do know that it's tough without something like that though, my sister who is also in the biz pays something like $700 a month for insurance.
Over the years I've seen a few groups try to get something going on like a group insurance thing for webmasters, but so far they all pretty much fizzled out...probably because of the multi-state problem.
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