Does the analysis change for you if you consider the difficulty of wrangling the important stuff for someone else in your family, should something untimely happen to you?

I used to do a box like this. The "temporal ordering" helped narrow search. But I found that finding things in it was still so difficult, that it wasn't worthwhile every time it'd be useful. There was also trying to find one document, and having to do a second thorough pass when I didn't find it in the first pass, which could take over an hour of misery.

Today, I routinely download and save PDF/OFX/QFX for every financial and insurance statement, as they become available. The few important paper documents I receive, go into a "to-scan" pile, which I try to clear out every few months.

(I really need to set up a scanning appliance/station that takes only seconds to use. I only need a to-scan pile because it currently takes about 10 minutes to set up for scanning and put things away after.)

I use temporal ordering for all paper financial papers I receive. I used to sort into folders by category, but the took too long. At tax time, I do a linear probe for the date range of the tax year.

Since Apple started providing better end to end encryption for Notes and iCloud, my wife and I just use that. We also have a ton of storage on OneDrive, so periodically I ZIP up important stuff, encrypt it and put on OneDrive.

>set up a scanning appliance/station that takes only seconds to use

Fujitsu ScanSnap is a highly recommended product. I have one on my desk that I bought over ten years ago -- it's slightly larger than a box of facial tissues (kleenex), all I have to do to scan is open the two "flaps", insert document, press a button, then assign a file name and folder (easy once a history list is established). Scans color or B&W, single side or duplex.

I use the same system! Never thought of it in those terms though. TIL it's essentially an analog write-only data lake.

A good book on dealing with the messy drawer and its contents is "Organise Your Paperwork: From Paper Mess To Paperless". Highly recommended.

Kind of a similar approach: one drawer for paperwork, google drive for all files, evernote for all notes with a dedicated notebook for different frequent used stuff like IDs, birth certificates, etc. Use search when I need something digital. Periodically throw away warranties and manuals from the big drawer (every 1-2 years) :)