Really hard to get medical insurance within the first two years when you have no records in the US, the firm I used, which did expatriate insurance, no longer sells in Florida. If you are buying a decent sized company one of the only ways may be to set up a company healthcare policy and put yourself on it, they are not so fussy then about medical records and about pre-existing. It is expensive. Ours has a big excess and just went up to $470 a month. I dont get anything at all for that, we pay for all doctors appointments, treatment, prescriptions until we have exhausted our $3500 excess. So it basically only covers serious illness or operations, like when I broke my arm last year. If we had no excess, I dont think I earn enough here to pay both my property tax and my health insurance. Start thinking about dental as well and you will talk yourself out of moving at all.