It’s an actual paper envelope kept in a safe. I can envision circumstances where I’m not dead but my wife may still need access to things. And if there were a service like that you propose, I wouldn’t use it. Working in cybersecurity has given me some trust issues.

That’s my plan.

I’m confident in my executor (my brother, if my wife isn’t available to serve) and in my children and their ability to handle this. My guess is that they would sell or otherwise dispose of things like books, tools, ham radio gear, and so on. And since I am not planning to leave anything to anyone else, I’m comfortable with the decisions they’ll make.

We recently ran into an issue where we had to make end of life decisions for someone who never told anyone what they would want, left no written instructions, and has been declared incompetent by a court. It’s far more complicated and unpleasant than I’m willing to share here, and it wasn’t fun to do. I took the opportunity provided by this lesson to spell out those things in my will, as well as to impart them to my close family so that there would be no misunderstandings. That’s way more important to me than who gets my favorite rifle.

I think of this as legacy planning, and it might include:
_what do you own?
(including stocks, IP, businesses, etc.)
-Who do you owe?
not just debts, but also any ongoing projects, contracts, etc.
-What do you want done?
Not just funeral, but also donations, gifts, destruction of super powerful rings, etc.
- Where is it all?
this includes passwords, bank accounts, etc.

If you can't trust your executor with your passwords while you're still alive, how do you trust them with your estate after you're dead?

Safe deposit boxes are good places to put sensitive stuff that you want to keep private until after you're dead. Put a paper sheet in there with your passwords if you're worried about it.
Just don't forget to document which bank you maintain the box at.

Best thing you can do is make an appointment with an estate lawyer. Most likely they will recommend you set up a trust and move the vast majority of your assets to that trust. Then you can set up co-trustees (who you want to have access now) and/or successor trustees (who gain access after your death).

Things like insurance policies should have your spouse (or whoever) as the beneficiary, and then the trust as a secondary beneficiary. Rental properties should be owned by an LLC, and then the LLC is owned by the trust. Bank accounts should be in the name of the trust.

An estate lawyer is not free. But they're worth it to set up a good estate plan (which if done right, can most likely keep things totally out of probate - depends on your state though).

Online access to accounts is probably not as important as you think it is. Generally, your executor can gain access by supplying a death certificate and documents that specify him/her as executor (usually specified in your will). It is important to have these accounts documented for your executor, but online access details are not as important. Often times when someone dies access to their stuff will be locked down as soon as the powers-that-be find out about the death. Being a co-signer on a bank account won't help one bit when the account is frozen due to the death. A trust-owned account with co or successor trustees is better. Another reasonable plan is to move money that is immediately needed out of their account before they die, or second best, before the bank freezes the account. Move quick. The executor will eventually gain access to the frozen accounts, but that takes a while and funeral homes want to be paid immediately.

As far as finding stuff after you're gone, good luck! It's a nightmare for anyone trying to do that. My plan is to keep "the good stuff" more or less gathered together for family, leaving the crap stuff to be spread over the rest of the house. Then have your executor advertise a free-for-all for the masses. Grab-and-go without looking at what you're grabbing is $1 an armload. Taking more than a minute to grab a bundle costs $10 an armload. Purposely digging around to find the good stuff is $50 an armload, decreasing to $25 an armload as the house is mostly cleared of junk. If you try to too tightly manage your junk dispersal - most of which nobody but you wants anyway - will end up with your executor having a house full of junk they can't get rid of, praying for a fire to sweep through and burn the the place to the ground.

Good subject.

It would also be wise to add (if seriously ill or injured; Chris Reeves(superman) comes to mind) type of scenario. I have seen people in bed for many years before they died.

Regarding envelopes, I have given my oldest daughter a folder that contains everything, and I mean everything , including passwords ..etc.

BTW, don't forget to give your family a paper folder containing a list of services (phone, electric and water bills ..etc.) . Every month, I sit at the laptop and log-in the bank account which is linked to bill payment service, and pay the bills. A guy I know went to prison, and suddenly his family found themselves unable to pay the electric bills because (a) they couldn't access the bank account, (b) they didn't had access to his phone (which receives log-in confirmations codes) ; the phone was confiscated as evidence. So, the family was paralyzed although the guy is still alive !!!

Sorry I'm late. I had to go help my sister clean out Mom's apartment after she died. Dad died in March, Mom in August.

After my wife died 4 years ago I rewrote my will then gave copies of the will, my master password to my password safe, a writeup of "my stuff", a thumbdrive with needed info and a key to my house to my primary (my sister) and my backup executor (an honorable former co-worker). I wear a dogtag around my neck with my primary executor's phone number (my sister - I have no children)

When my wife passed I learned the value of our password safe routine such that I had all her passwords to every account and could make needed changes far more easily than if I'd had to provide a death cert for everything.

In my Dad's case I had his passwords for email and Facebook so as he was fading out I could advise his huge number of friends of his deteriorating condition. I got back many, many notes of condolences and remembrance from those folks that I could read to him over the phone (I couldn't visit because I hadn't been able to get the vax yet) before he passed so he knew he was loved and respected. The most memorable was a quote from an old Naval Aviator and friend of 50 years who said "I'm going to cry myself to sleep tonite."

I recommend having a plan and having trustworthy people to execute it for you.

Being alive has given me major trust issues.

With accounts and passwords on paper in a safe, how often do you have to update/reprint?

I've been wondering about a dead man switch type of scenario https://en.wikipedia.org/wiki/Safe_House_(1998_film)