Hi cjwidd, so here's how I would recommend constructing your shape to get better quality geometry which will help with filleting.
So to start with your base profile curve should be as simplified as possible - every piece of the profile that is in the shape of a straight line should just be a simple 2 point line curve and not a lot of smaller segmented pieces:
Then use Construct > Extrude with "Both sides" option to make your base shape:
Now you want to use the other profiles you've drawn in the Top view:
Select your extruded piece and run Construct > Boolean > Difference, then select your 2 top-view profiles as the cutting objects.
That will slice your extrusion up into 3 pieces, discard the outer pieces and you'll be left with your result:
So notice there how the whole process was driven by 2d profile curves, and the final curved edges are a result of doing a boolean with the first solid against another 2D profile curve. That's usually the best way to do things, you don't want to try to build the 3D curved edges first and try to patch things between those piece by piece for mechanical parts, that's something that you'd only use for more semi-organic shapes that aren't well defined by 2D profile curves.
So then with this cleaned up result you should be able to fillet it although another fillet "gotcha" is that it can be surprising how much space fillets eat away from the model when curving pieces are involved. For your case here you will only be able to go to a maximum of 0.04 units before fillets in this area of the model will start to run into each other and cause the fillet to fail:
So you might want to leave the little circle out and cut that out with another boolean after you've done a larger radius fillet across everything else.
Hope this helps!
- Michael
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