You should be able to get health insurance for less than $1800 a year, so that appears to be a no-brainer at this stage. I have health insurance, but that is more due to inertia than real planning. A few years ago, I decided I was in the wrong insurance (basic rather than top cover), because most of the things that would cause me problems weren't covered. I found a top cover that was cheaper than the basic cover I was in. A few months ago someone was talking about how expensive their cover is, so I looked into mine. It is still cheaper than any I have found elsewhere, but it has closed for new entrants, so that is one reason I am keeping with it for now.