What do these cron jobs check for?
So OP has to regularly do some action until they can't (either aren't able to, or are dead in this case).
Touch a file on login.
Cron checks if file is X days/months/years old. Also I would add two offset. First triggers earlier with reminder to self (taking extra long holidays while forgetting about cronjob), second is actual dead-man-switch when you are probably incapacitated or dead.
And in that ensuring that all your legal matters will be easy on your family.