Re: Documents folder
Cannot speak for OP, but for me I never trusted the folder because it was longer than 8 characters. Back in the day when Windows 95 came out they encouraged you to put documents in the My Documents folder.
When you enhanced* to DOS and did a simple directory listing the folder appeared as MYDOCU~1 or the like. This made finding the folder programmatically a nightmare. Following on from the nightmare, any code that was written to copy or backup your files may have caused mangling of the filenames you selected, or missed them outright.
In my mind, the original purpose of the My Documents folder was to show the world that Microsoft had finally caught up with the likes of Unix and could now happily support any filename you wanted while still elegantly being backward compatible. Nothing could have been further from the truth. It wasn't until NT, and for the majority, Windows 2000 till Microsoft could actually claim long filename support.
This whole theory was given much more weight when the My Documents folder was renamed Documents. I mean really, who cares who's documents they are, you just want to know they are documents and not programs. Also it would be good it they could just stay where you left them and not be deleted randomly.
*"Dropping to DOS" is an example of the double speak people will use to cover their attempt at perception manipulation for increasing sales. You were never "dropping" to DOS, you were invoking a shell and getting real work done. Looking at Microsoft shell support today, it feels like the world wasted 20 years unnecessarily clicking OK.
See a video of the Xerox Alto in action for what computer systems were based on. Windows and Mac were developed by "copy what you saw there" and not like Xerox, iterate with purpose and unlimited funds until success.
Herein lies the problem, copy what you saw being done vs invent and continuously develop a working solution to the problem. Copying and forgery are probably the worlds third oldest professions, so this cat and mouse game is not going to change.
When there is was only one telephone in the world there is not a lot of point having one, it takes many to make the system work and be of value to anyone. Thus, a bunch of Altos were made and plonked on desks the world over. They were all connected by a new fancy thing called Ethernet.
This led to fierce competition between players of the Alto program Maze Wars. This competition and code level cheating caused consternation for the authors as they were getting complaints about cheating. This led to the invention of secure source code repositories and obfuscated executables.
Necessity is the mother and without some need invention will not occur. It is not until you encounter someone who will not play by your rules that you need to enforce rules or alternatively just play another game.
MYDOCU~! is a game we should not have played, but who were we to know and what could we have done to stop it anyway? Was the 8.3 limitation was imposed by costs and computational limitation at the time DOS was written, or was it a function of hiring ex Xerox employees and this is the rules they were used to?
In the 1990's I must have typed ATZ a thousand times. It wasn't until recently that I realised that I was connecting with the ancient and well organised people at the dawn of the computer age. So as a shout out to the wonderful people who were at Xerox and the made everything up to and including the Alto: