Hi JL, please see attached 3DM file for a strategy that will work better for filleting.
The steps I used were like this - I made a profile curve like this:
Then I did a sweep using the longer neighboring edge as the rail curve:
That makes a surface like this which has much better quality than the previous ones there, it's not awkwardly pinched together which is what you will get if you try to do something like a Network surface to an irregular boundary:
Then I used Edit > Trim to cut away these pieces:
Then use Edit > Join to glue those remaining pieces together and you should now be able to fillet like this:
Hope that helps, - Michael
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