Jørn-Harald Paulsen shares a Maya script he created and some insights into its use. The Cartoony Wheel Rig Script will create a sig for a wheel that will allow for some cartoon like squashing and stretching, and although Jørn-Harald calls this a work in progress, you are still able to download and use the script.

…When rigging vehicles you’ll usually have to deal with at least two wheels, and (especially if you’re going cartoony) you’re going to waste a lot of time if you’re rigging them manually, one by one. So I decided to write a script for this, the script is supposed to do all of the work automaticly, and it should work with wheels regardless of size an position…

The Cartoony Wheel Rig Script for Maya also has a contact controller that deals with floor contact and two controllers for wheel rolling, and another for translation, rotation and scaling.