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An S-corporation and a good tax accountant are the way to go. Corporate filing fees in FL are $150/yr, and the advantages on income tax are absolutely stunning. You have to do the sales tax paperwork either way. Nolo press has a book on incorporating. Follow the instructions in it and save a few hundred and a whole lot of hassle.
As for health insurance in Florida - good luck. Unfortunately, the state has a perfect storm. It has many many rich retired seniors that go to the hospital for every ache and pain, a large population of poor who depend on hospitals, and lots of fraud in medical practices. Insurance rates are among the highest in the nation, and you won't be able to get a decent group policy, much less a decent one at a decent rate.
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