Another thing that makes for difficulty with filleting is when 2 surfaces are fairly close to being smooth to each other but actually meet at something like a 5 degree angle. When surfaces meet smoothly then it also means that fillets traveling along that area will also meet up smoothly. When 2 surfaces meet at a sharp angle it means the fillet surfaces do not themselves naturally meet up end to end and instead need a corner juncture patch to be made. But when they are pretty close to being smooth the juncture piece may be some little slivery piece itself which things have difficulty processing.
Here's one such area along where you want to fillet that looks like it is not quite smooth but at a very shallow angle:
It would be a lot more "fillet friendly" if that was a whole smooth edge there, probably with those pieces being one single surface rather than 2 separate faces.
- Michael
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