Directory Opus was and is THE best file manager. I have been looking for one in Windows for years, but the best I found is Magellan and that is shite!
Deluxe Paint is what I learnt graphics on, and TG is right on what is sadly lacking in Photoshop 6. Even mega-buck programs like Maya and 3DS Max are not as friendly as their PC rivals.
BTW in Photoshop you can define a brush as a pattern and fill a selection or the screen with it.
I used to use Textpad on the PC to write my code, now I write it in CygnusEd and then port it to the PC for testing in MSIE. Bad way of doing it, but CED is just a programmer's text editing dream.
Finally to CLI/Shell. Absolutely pisses over MS-DOS, but I'd say that Linux console (pah! who needs KDE/Gnome!?) is better and far more flexible. Shame the editors are so crap.