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I'll +1 your gripe with my old man yelling at clouds thing. Windows XP gave you the option of creating arbitrary taskbars/toolbars to locations on the desktop that could be floating or docked. I have always kept my data on a separate drive or array from the one my OS lives on. In Windows XP I would create a toolbar that contained the root of my data drive, dock it to the right side of my monitor, and then set it to autohide the same way you can set the taskbar to auto hide.
That in conjunction with the way that Windows XP allowed you to remap "My Documents" to a different location made for the cleanest workflow I have ever had.
They removed the toolbar functionality after XP and changed the way remapping system folders works slightly since then. I haven't really found an application that gives the exact same functionality as the arbitrary toolbar from XP, but even if I did I still spend over half my day at work on a computer that is locked down by corporate IT where I can't install whatever I want, and I like to try and mirror workflows between home and work because of muscle memory.
I'm in my mid 30s, lol.