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I suspect he may have had encrypted his notes/HDD and with his death the information was lost.

What reason do you have to suspect this extraordinary measure?

I have seen it happen and know of several cases where large amounts of valuable data was 'lost' until someones password was cracked.

PS: Escrow services and wills are something that many people don't use. It's the old if I am gone I don't really care mentality.

It's like a two-step procedure on OSX. Hardly extraordinary and most likely an obvious first step on machines that will contain patient records.