I think that's entirely up to you!
As for the underlay matching the laminate, what do you mean?
You should leave an expansion gap for the ply, same as for the laminate, though admittedly it can be smaller since it's nailed down. The underlay is compressible so it doesn't matter if it runs up the wall or not, it won't stop the hard stuff from expanding. Having it run up the wall, behind the skirting, can be a good thing to help block draughts, though this doesn't apply in your situation since your skirting is already fitted, of course.No!
What I meant was, rather than trim it and leave an expansion gap, take the edges up the skirting just slightly, then nail the ply down and trim the bottom underlay so it is level with the top of the ply. Presumably, as the ply is thoroughly nailed down, you don't need to leave an expansion gap and can trap the underlay 'tween ply and skirt?