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at what point should one get health insurance

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I've posted before that in a few years time my wife and I might be able to travel for long periods of time in Europe. Others have mentioned the importance of having valid health insurance for this, as usually one's US insurance won't be valid. My question is, if one should get special insurance for a long trip, say of 3 months, what about a short two week trip like so many US visitors take. Shouldn't they also look into this? What should be the cutoff for the trip length?
It does seem ridiculous to get health insurance for a 14 day trip, but if one should get covered for a long one, why not a short one?

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