My two cents,
Until fairly recently these were cut with core box bits (round nose), they are still available. The Bowl and Tray bits are better suited to manual use with templates
That is looking better. You definitely need to do some test to get the surface finish you want without spending all day carving. With that shape waterline might be real nice.
I wonder if you could just make it a simple 2d slot? Then using that bit you should end up with the shape you want at the end. Will just have to set the depth for what you are looking for and the width correctly to trick it into thinking its a normal bit.
I went back and re read your original post. I didn’t catch that your bit wasn’t the same radius as what you were trying to achieve. For that you are on the right path with 3d milling. Probably just need to lower your stepover on the finishing pass. Probably by at least half of what you used. Will make it take longer but it will give a much nicer finish.
Yup. This method can get you super crazy detailed cuts. It is worth doing a few test cuts. It is what I believe to be one of the only things a CNC can actually do that you can not do by hand without years of skill building.