I don't have a highline display so I'm not 100% but I doubt it will.
Also as far as I know you just put the SD card into a PC download the Sygic software and it will update it. I've never actually done it though. I've been really happy with it for the past two years though. The only thing that lets it down is the iPod menu. It only shows a list of all the songs and no selection for Artists, albums etc. It's not too much problem as I mainly use the SD card though or if I do have the iPod on it's on shuffle and I just skip through.