Ok so after slaving hours upon hours on painting the weights, I have come to the sad conclusion that I will probably not be able to accomplish what I wanted to. The automated rigging system that was suggested for us really did help a lot, and I thank Steve for suggesting it. But I really wish I organized things a little differently in terms of the progress, such as making a low poly model in Maya first THEN going into Mudbox to work on it. This would cause painting the weights to be even easier, so it saddens me I didn't do this.
In light of this I believe it's probably best to just focus on making the model I created even higher in detail, and then fully texturing the model. I also believe it'd be good to just focus on a separate even more detailed version of the head along with this.
I will however still try and give off the illusion that it was created with plasticine, which, with the proper texturing and lighting should work perfectly (I hope!)