There is certainly no reason that you can't! All of the tools except Illustrator are free, and there are certainly vector drawing programs that you can use instead that are open source. (Inkscape, for example.)
Everything that I do here you are more than capable of doing yourself. It's just a matter of beating your head against the problem until it falls down.
RE: [3D and Illustration] Making Game Tokens For Tabletop Simulator