I'd say it really depends on what he plays... from what i remember, i preferred the roland cube for high gain stuff (tell him to avoid the 15 and 20 watt versions, as they don't have as many (if any) amp models), while i preferred the vox for more vintage tones. To me personally, the cut-off was 80s rock/metal- anything 80s rock/metal and heavier i preferred the cube, anything lighter i preferred the vox.
Though if he plays an equal amount of both, i'd prefer the cube, as i wasn't too fussed on the vox's high gain tones (there's a new higher gain vox valvetronix out, but i haven't tried that, and i've heard mixed reviews)...
just in my opinion, and bear in mind i've never owned either, that's from faffing about in a shop... EDIT: i'm not sure about headphones either- i'd assume they have them, but i wasn't looking into that. Not sure about drum patterns either... :lol: