Hi eric!
First thought in my head is that Zbrush would be a better tool for that, even if you want a very stylized result.
Now, for your specific situation, there are instances where fillet and chamfer will not complete successfully because of the specific geometry of your object. For example, for a fillet command to completely process a series of edges, it needs to have the necessary distance from nearby edges to create the circular profile. From my understanding (I am new to MoI) as things get more cluttered and geometry becomes more complicated, completing fillets on a whole object or even a series of edges becomes more difficult. Sometimes, merging edges (using the merge command) and picking small groups, or even selecting a specific surface might give you a better chance. When the fillet command fails to process your selection it sometimes creates a profile that with slight modifications can be booleaned or used as a trimming object so you can get something close to what you were going for. That's what you are seeing in your example.
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