Does insurance really cost more the later you buy it?

The cheapest time to buy an insurance policy is the day before you suffer from a mishap or a critical illness. Of course, this is assuming that condition does not fall within the waiting period. Otherwise, you will need to add an additional thirty to ninety days before you buy. That is for the sake of answering your comparison question.

Be that as it may, this also depends on your risk appetite and how much risk you wish to retain vs transfer to the insurance company. The more risk you are willing to undertake yourself, the lesser insurance you need to buy. Consequently, the more savings you have.

However, the moment a catastrophe strikes, time value of money has a negative value now.

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