For this milestone, I feel like I've made some progress to be happy about. Per one of my advisors advice, I took some more time to develop the look of my town and characters. Since I want this to have a more stylized look, I think it's good that I have something to reference now. I also took a bit of time to create a new 3D animatic of what the new story is going to look like. The time is nearly cut in half and is now limited to 3 simulation shots with some other character animation in between. This to me seems to be a lot more manageable. I worked a little bit on the modeling for my main character, specifically with the arms and hands. I found a look that I think I like and got over my mental hump of how to do the shoulders (I just added little sleeves to make his top a polo). If I decide later on I don't like the look of the hands, I may switch to something way simpler (little cylinders for fingers coming out at the end of the arm). I may get some feedback from friends and family on that one. Finally I did some research and am going to do 2D mouth and eyes for the faces of the characters. I think this will fit the characters and make the style more unique. I also think it may be slightly easier than figuring out how to make 3D mouth bag.
By the next milestone, I want to finish my character models down to the finer details and work on a usable expression sheet to experiment with animating the face. I'm feeling good now and am ready to solidify these characters. 
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