One or two pass for a fillet?

Hi everyone, I am new to CNC machining. My machine is very small, a tormach 440. I was wondering, I have a very small fillet (r:1mm) that is at the floor of my part. I was wondering, should I do this in one pass with a 2mm diameter ball end mill, or do multiple passes with a slightly smaller tool, say 1.8mm diameter? What kind of strategy should I use for the tapered section just above the fillet? Thanks y’all.

Depends what this part will do. If either of those surfaces are contact it really depends on the tolerance of the part contacting them. If the tolerance is to close and a button is pushed into that reducing diameter it’s going to bind at the bottom.
I would use a bullnose end mill whatever that radius is if possible. It looks like the reach is between 3-4 mm deep and that’s the length of most 1mm end mills. 1.2mm should be fine but 2-4 mm with a matching radius will do the exact same thing at twice the speed.

As far as the taper a slope tool path should be fine. Use a bottom up path for finishing the taper and fillet.