What do you do for health care insurance

My wife and i are 54 and 44 years old. We would like to full time why we are still reasonably healthy. One of our biggest expenses would be health care our premiums now are $1240 a month( paid for through employment) with what I feel is very good coverage with low deductible I do have a blood disorder where as I need to have it checked monthly in order to get my pills. We do have some rental property that nets us about $6000 a year after expenses, a home that is paid for that could be rented out and contribute that income to our IRA not wanting to sell at this point. I.R.A.'s and stocks that equal about 4 years of our gross income ( we do not want to touch this) we would like to be south in the winter north in the summer. Would like to work say 2 weeks on 2 weeks off. My wife has book keeping experience as well as a D.S.P. for mentally disabled. I have management, sales, experience and CDL license. We would have years income in the bank as start up money. We would need to secure health insurance and would like some suggestions. Also do you think it would work I would not draw S.S. for 16 more years if it will even be there then wife has longer to wait. What do you think just trying to get a plan together as would like to do this in the next 24 months. Any information or advice would be appreciated.