I really depends on subject and app
It really depends on three things:
a. What kind of object you are trying to create - as you say Del, AI is good at somethings, Photoshop others.
b. What software you possess and/or which app you are most comfortable with. While I might use Xara for many types of objects, someone else might prefer GIMP to ever using Xara - it depends on what you like to work with.
c. Finally the map style - if you're going for a hand-drawn map, using 3D tokens clashes in style.
This is the problem I'm having with my July Challenge map. I created a Xara photorich map design, but I don't have ready 3D models to place as tokens, I may end up drawing them by hand, however doing this is a clash in style.
The tokens I create are either 3D models rendered as top downs, hand-drawn works or Xara created...