The case that has bugged me is when I have some integer number of items and I need to compute some CGFloat for drawing something based on it. count * SpacingPixels gives an error, need CGFloat(count) * SpacingPixels even though there is no possibility of losing precision by the up-cast from Int to CGFloat.
It is also slightly annoying to have Double and CGFloat not be the same, but I solved that by just always using CGFloat pretty much everywhere even when not referring to pixels or points.
I don't think I would overload + and *, though, due to possible complications with the error messages as the article suggests. But I might play with more terse Ruby-like ".to_f" as an extension or something ...