The manual checking in part seems like a lot of hassle, even if it's only once every 2 months or so. If I wanted to have something like this, I'd want it to be as set-and-forget as possible.
For example, me being alive could be determined by whether I logged into my machine over the last X days and a certain service ran. If it didn't, only then start bugging me to confirm manually.
Also, as others have already mentioned, I'd have very little trust that such service will still be around when I'll need it to trigger.
Something like scheduled gmail + a cronjob on my local machine that runs once a day and reschedules the email is something I'd imagine could work if I wanted to set up something like this for myself.
What is the rule that says something in the lines of: if you don't verify your backups you don't have backups.
I feel that applies here, this doesn't need to take more than 10 seconds once a month (at least I would prefer it to be often enough that if it didn't come I'd recognize something was off - anything more than a month and I'd probably never notice if they stopped coming).
Each verification also serves the purpose of reminding you the service exists, that it is alive and at least gives you some indication and confidence that it will work when you want it to (also makes you think about it, after ten years maybe you'd want to update the content for it to still be relevant).
I’ve been using DMS for years and think it’s excellent. It’s not a hassle at all: once a month, I get an email and all I need to do is click on the link in it. That’s it.
Also, I use it to email only one designated person who receives an email with a password hint to an encrypted folder containing all my important stuff in life such as passwords etc.
I don't know about that, things don't get automatically cancelled just because someone dies. Most likely it'll take weeks or even months before the payments will be denied.
For example, me being alive could be determined by whether I logged into my machine over the last X days and a certain service ran. If it didn't, only then start bugging me to confirm manually.
Also, as others have already mentioned, I'd have very little trust that such service will still be around when I'll need it to trigger.
Something like scheduled gmail + a cronjob on my local machine that runs once a day and reschedules the email is something I'd imagine could work if I wanted to set up something like this for myself.