I think I finally have the look of Bob.
The placement of the eyes allows for a wide range of expressions while also keeping him somewhat oblivious. Sheep have a long snout as it is, and it makes for an easy cartoon to simply place it way out. Keeping the mouth in closer feels right to me because then I'll be able to stretch it out to the end when needed.
And to think the very, very, very first incarnation of Bob was this.
Yes, Bob was originally going to wear tennis shoes, but not any more.