Nobody likes dealing with passwords. Or death. Or taxes. What all three have in common is what your loved ones will have to deal with when you are gone. If you think your password situation is difficult for you, imagine how difficult it will be for someone else to figure out without you.
I recently had one client whose daughter died. Because she gained access to her daughter's Facebook account, she was able to experience the outpouring of love from hundreds of people who were deeply touched by her daughter. Many of these tributes were written by people that my client had never heard of.
Another client's husband died. I was asked to try and access the important financial business data that seemed to be well hidden. Although her husband had left her a sheet of passwords, none allowed her to unlock a protected folder which we suspected had these documents.
It is common to hear my clients say that passwords are the bane of their existence, and most are frustrated by them. I see many methods of keeping track of passwords, from using the same password for everything to taping them on the front of their computer. I recommend using a password manager, a program that stores all passwords in a safe (encrypted) form. A single password unlocks access to all the other passwords.
Although using a password manager is not uncommon, there are two basic keys to making this strategy a successful one after your own death. First, your master password (the one that unlocks the program) must either be in the hands of the person or people who you want to have it. With some password managers, presentation of a death certificate can trigger the release of this password to the assigned beneficiary. However you want to deal with this issue, it must be acted on in the present, not the future. Planning to pass on a password is great. Having an effective mechanism in place is a necessity. Without getting too metaphysical or maudlin, these arrangements need to be done before it is too late. Like backing up your computer, it must be done before you need to.
The second issue is making sure your password manager is complete and up to date. I help my clients create and record their passwords all the time. It is a process that is never finished.