Countdown Delay (Dead Man's Switch) to send e-mail

[Antitheon]

I need a way to send a couple dozen e-mail messages on a countdown timer in the event I'm unable to do so. You could probably call it a "dead man's switch" because I'd be using it to cover the possibilities of incapacity or death.

I've been in a gradual decline due to an auto-immune disease for some time now, but a routine doctor's visit revealed an unexpected acute threat just a few days ago.

I was told I could have died that day.

That's not nearly as scary as it sounds (scarier for my poor doctor I think ). I've been sick long enough to adjust to the idea, so nobody waste any pity on my account. We all gotta go from something.

However, had things gone differently there would have been a lot of final correspondence (thank you letters, mostly) that would never have been sent. Gradual decline had at least offered me the luxury of knowing when it was time to write them. Now I can't count on that.

There are a few letters I've already written handed off to a friend to post for me in the event. There's also the legal machinery of my will to handle some things. However, I'd much prefer to handle the more basic thank you and regard notes via e-mail -- by myself -- because they can be updated a lot more easily than pre-sealed, pre-addressed, pre-stamped envelopes.

So what I'm looking for is a way to send a bunch of e-mails on a 30-day delay that I can push back every time I log on. I've been experimenting with Boomerang, but the 10 message limit and the method of rescheduling seems a little awkward. I need to be able to push back the timer easily even if disabled or hospitalized.

Does anyone know of any other service that can perform a countdown delay to send out final thank you/regards? I need something that will work on the server level, like Boomerang, but better suited to work as a countdown delay.

[Panzer]

I found these:

http://www.lettermelater.com/
https://addons.mozilla.org/sl/thunde.../send-later-3/
https://www.streak.com/send-later-scheduled-gmail

[Antitheon]

Thanks, I'd missed LetterMeLater.com.

Looks promising.

Will report back on LetterMeLater vs. Boomerang after testing.

[Ritho]

Just thought I would mention here that gmail has a little known built-in feature like this. Unfortunately the shortest period for the time out is 3 months which might be a little too long for your purposes.

You can set it up to send out emails, or even give access to parts of your account or certain data to a trusted person. You access it by logging in to your gmail account then visiting https://www.google.com/settings/account/inactive

[Panzer]

One more:
http://emailfuture.com/

[Sope]

I've just tried out https://www.futureme.org/
Straightforward and simple.

Only problem I can foresee with these types of service is you have to trust them with your email address. Also I wouldn't want to put any personal details and suchlike in the message.