Have you seen this site http://www.freelancersunion.org/? They have a lot of information, for you, right now, I would reccomend reading this: http://www.freelancersunion.org/insurance/index.html

http://ehealthinsurance.com

Check it out. It's for people like you who can't get in on some group plan.

As a freelancer you will need to apply for an individual plan. If you are young and healthy these are often the most affordable plans. The problem is that with these plans you can be denied when applying if the insurance company does not like something on your application. In most states if you have two or more people (the other person can not be your spouse) that have a business you can apply for small business group health insurance. The big benefit with small group is that it is normally guaranteed issue which means that the insurance company can not deny the group's application. Small group plans have many more options and plan designs but in some cases may not be the cheapest option.

Health insurance is regulated by the states so it really depends on where you live, but the previous posters are right about how you can apply for individual insurance, but you might get rejected. Many states have good options (called "Risk Pools") for people that don't qualify for private insurance. Check out this site to see if your state has one of these Risk Pools: http://zanebenefits.com/blog/2009/08/154/A+State-by-State+Guide+to+Guaranteed+Issue+Individual+Health+Insurance

Assuming you can get individual insurance, the next step is to set up a Section 125 (or POP) plan so you can pay for it tax free. This could save you up to 50% depending on the tax bracket you're in now. POP plans have only recently become legal for individual insurance so there aren't a ton of companies offering them, but you should be able to find something if you do a little googling.

I'm pretty sure that you can only get traditional group insurance if everyone in the group is a W-2 employee, so I don't think that a bunch of freelancers could join together to form a group plan. Also, insurance prices are heavily regulated and I'm pretty sure that insurance carriers aren't legally allowed to offer discounts, so a group of people buying individual insurance policies wouldn't be able to get a lower price I don't think.