Growing up with Pre-OSX makes me think that there wasn't really much to learn about OS9. It felt much simpler than OSX, but looking back at it, there are definitely many tricks to mastering the old system.
A few features that I always admired about OS9:
The Spatial Finder - one icon = one file, one window = one folder, no ifs, no buts. There is no such thing as having two windows of the same folder open. This sounds limiting, but it was a solid underpinning of the Mac OS foundation. Move and resize a window and the OS will always remember the size and position of that window, because "the window is the folder". Finely Position any icon and that's where it will be next time you look for it. I really love this concept, but I don't think it would work well in OS X.
Popup / Tabbed windows - drag a window titlebar to the bottom of the screen and it becomes a popup tabbed window. Similar to having a folder icon in the dock in OSX, but again, the window is the folder, so it is technically "open".
The Control Strip - one click and all your accessible settings are hidden away, unlike the multitude of menu icons in OS X / macOS.
Custom Icons EVERYWHERE.. don't be shy, download icon packs then copy and paste custom icons onto everything.
Window Shade! - Switching back to OS 9 makes me admire this simple feature. Be sure to enable the "Double-click to collapse windows" option in the Appearance Control Panel.
A couple of little things to keep in mind;
* Install
Classilla
* If an application seems to randomly crash, or crashes on launch. Try assigning more memory by choosing File -> Get Info, then upping the Preferred Memory option by a few MB or so.
* Click and drag down on the applications menu on the top right to get a floating panel of open apps. Click the zoom widget to view as icons only, option-click on the zoom again to switch between small/large icons, finally, option-shift-click the zoom to change orientation of the panel for a dock-like row of icons instead of an app list.
* One simple trick that will resolve almost every "Cannot find the Application used to open this file" type errors:
Hold Command+Option before your drives appear on the desktop and choose "Rebuild Desktop".
(There are dozens of little tricks like this using modifier keys for different 'secret' features. Try looking for a cheat sheet on Google.)
I'm sure many others would agree that OS9 is pure nostalgia and really just fun to get back into that space. But every time I decide to take a trip down memory lane, I find it cumbersome to get any work done. Even word processing can be limiting as shortcuts that I've come to expect are just not there in OS9. If you want to tinker however, you can use ResEdit modify and add your own keyboard shortcuts to almost any menu item in any application.