Can someone explain to me once and for all why I can put asterisks in mac filenames but not windows

@equium IIRC. In windows * is the "wildcard" symbol. So if you want to do a search for all .png files, you do dir *.png

If you know it begins with "furry_" you can do a search for furry_*.png and it'll find everything in between.

Couple of other things from old DOS days that you can't do either.

https://www.youtube.com/watch?v=bC6tngl0PTI

Why You Can't Name A File CON In Windows

YouTube