Rich_Art,

The two problems I'm seeing is that, not only are some of the areas you want to fillet too small for the sized fillet you desire, but I think the fillet tool is having a hard time 'seeing' around that seam below the pointer notch on top, above the button's top surface.

First, I would try filleting both the pointer and button body objects separately, then union-ing them.

Second, you might want to attempt a manual fillet procedure: http://moi3d.com/forum/index.php?webtag=MOI&msg=4607.5

Using your edge curves to act as paths for swept circles, which are used to difference an offset of material away so that you can re-build with blend surfaces.

But try to fillet the main objects separately to bring the complexity down.