There are basically 2 problems here: there can be a visible "edge" or
"ridge" to the paint you cut in. When it dries, the roller coat goes over
and the ridge is still visible. Or, there could be a color problem, where
the cut-in paint right next to the wall is a little lighter than the seam
where the cut-in and roller overlap (2 coats darkening slightly.) This is
not going to be a problem when using 2 coats, but with 1 coat and good
paint, if the cut-in is painted too thin the color might not be right when
they're overlapped.
I usually cut-in all at once, and feather the edge so there's no ridge. The
trick is to keep the cut-in thick enough so that the color matches the
roller paint, but no so thick that I start getting sloppy with the corner
edge. What do others think?