Should I pay insurance premium yearly or monthly?

Cash rebates should not matter any more as insurance companies come under the Financial Services MCC which is more often than not, excluded from receiving rebates.

Answer: Yes it is cheaper to pay annually as insurance company gives some discount for lump sum yearly payment.

​

However, income only accept 1st payment via credit card, subsequent all has to be in the form of bank transfer / cheque.

(Source: https://www.income.com.sg/contact-us/premium-pa...)

​

So your policy is with the rest of the company and they allow credit card payment, it does have the benefits as you've said to:

charge to credit card via monthly payment to be counted towards minimum spend and with the right card (cashback/miles), you can reap your rewards (like what Jin Shun Chia said below is a good strategy).

​