I agree; rolling the edge of the fretboard before the frets are in simply makes the ends of the frets stand MORE proud, which works against the whole idea of rolling the board.
I typically use Micro-Mesh pads to break that corner after finishing up the fretwork, polishing until the ends of the frets are rounded and smooth, and the sharp corner of the board between the frets is slightly softened.
That general approach is what the edges of fretboards and frets should look like for best playability. The extremes of them not being this way, and a poorly cut nut, are the overwhelming factors resulting in a guitar that feels like a "cheap guitar." Do this to any old "crappy" $150 guitar (along with the installation of a hand cut nut), and it will play better than a new Gibson.
I've heard lots of online people complain about strings pulling off the edges...but that's just a sign that someone has done it wrong. If done properly, there should be a very minimal, if any, difference in how deeply the fret bevels go in from the ends of the frets. They just get a hell of a lot smoother to move over.
That does look pretty . . . although I haven't run into the undercut fret ends thing you're talking about. After rolling when you finish refretting the dressing you give to the fret ends is maybe slightly more involved with rolled edges (you've got to round the fret ends a bit more than you would otherwise), but ends up being very comfortable to play.