1. Wine in the room all the time. If I am staying for a few days I usually go on a supply run after checking in. Wine, ideally something local, is on the list.
2A. Hotel bar/restaurant? Bottle maybe but expect corkage fee. I usually ask about this first. Glass no...but I confess I did do this many moons ago when I was much younger/poorer/cheaper. Half the time a waitress would come up and ask if we wanted a refill while stating they "forgot" what we were drinking.