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For me it's not the cost savings of the insurance that's the issue. It's the issue of being on an individual plan. Legally an insurance company can't cancel my policy because someone covered needs expensive ongoing treatment for major illnesses but they can legally raise my monthly rate to $1,000,000 if they choose. Most states offer protection with group plans but not individual plans. That's the only reason I'm interested in group health insurance.
The association could be dedicated to small web based businesses. Basically anyone that doesn't have a store front but sells goods or services on-line.
The association could also negotiate discounts with legal services, hosting and software providers. As some people have pointed out NY and I think New Jersey are different beasts and may not qualify for a national group sort of thing.
Finding 1,000 webmaster may be tough and then you need to find someone in each state that's willing to handle the paper work.
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