re: Hospital indemnity insurance question

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1. Before cancelling, should he bother attempting to claim his recent hospital stay and hope that the company (Guarantee Trust Life Insurance) uses discretion to allow him to file months beyond the provided time limit? His plea would basically be "I didn't know the extent of my benefit."

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I would file anyway under the "or some similar reason, as soon thereafter as is reasonably possible". The worst that can happen is they deny the claim. But, it would be better to have a quick consultation with an attorney that either specializes in elder law, or medical law. Being mindful of how much he would actually be able to collect vs what it would cost for the legal consultation

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2. Is it possible that he's been overpaying for his premiums all this time? One box says that his annual premium is $40.70 while the next box seems to say $40.70 monthly. Which is it? (He pays that monthly.)

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In looking at the form, I read that as he is agreeing to pay the annual premium on a monthly basis. So, it would actually appear that he has been overpaying and could have a hefty credit that may cover him for a few years of "prepaid" coverage