OS4 has made some progress on fonts by unifying all (most?) outline font types under a single TypeManager/Intellifont/Fountain-like program. On OS3 we still need separate font install utils for TTF, PostScript, Intellifont, etc. So step 1 would be bringing a similar unified utility to OS3.
Step 2 would be better font family detection across the board. I'd like to see ASL font requesters display, e.g., just Arial and not all of Arial, Arial Bold, Arial Italic, Arial Bold Italic, etc. The subtype should be selectable from another gadget in the requester. And if I have a font and I set it to be italic I want the system to automatically use the italic variety of that font, not apply some algorithmic distortion to it.
Step 3 would be the ability to drop some .ttf or .otf files into Fonts: and have them just work - without having to "install" them.