I have never had to use my zen on linux yet I have a wireless dock, I charge an upload new files with that.
I haven't used a HP printer with linux as yet I print my stuff off over my network, the only printer brand that i know of that has problems with linux is lexmark sad reely as I love them very cheep ink an affordable quality.
Wine adds a compatibility layer to linux that allows a windows program to run under linux, I havnt had much gaming experiance under linux as I don't game any more but I am getting a hankering to play Fallout tonight ao i might give it a shot.