My Plan for Retirement was to accumulate a Portfolio of Rentals and then fix them all up to Sell one off every two years and go surfing and sailing and take care of my Health.

Bill's allusion to "illegality" may be based upon the health insurance industry and his correct reference to the negative issues forming of a group for the sole purpose of purchasing insurance in such a manner.

One thing you can do is call the Health Department.

They have strict guidelines to remove money which is almost impossible to remove (with exceptions like health conditions, primary home etc.).If I change company will i be able to get that 401k money.

I want to enjoy whatever years of life and good health I have and am happy to spend my money on things that make me happy.

If you did one big one and you wanted to reduce coverage, would you still be in good health?   

I came to this place as I am selling a property in Australia and buying a rural property for a Health Retreat.

I agree with your thought process in that besides from my REQUIRED reserves, I should really be basing any additional reserves on the "health" of the property prior to making the purchase.Dan

Assesses his profit and business health regularly.

Planning ,   Public works  if its a private water company or public company check in with them to determine sizing.and the fire departments in many areas have minimum fire flow rules for subdivisions  1,500 GPM at the hydrant  Architect would be someone you would hire to actually design your buildings that is farther down the line.. you need to understand what is possible on the property.Or the health department for minimum lot size when served by septic and public water or septic and sewer.. and just bust it up in lots and sell off .. good thing is your fronting public streets already so it could be as easy as taps into the public water and putting in septic tanks and drawing lines for your new lots which a civil engineer would normally do.. you may never need to ever talk to an architect unless your going to actually build something.