I bet all the major cities that were there 1000 years ago (from skyrim's time) will be in the game this includes MWs OBs and skyrim and perhaps the older TESs
Yeah, probably. You could even check through the http://www.imperial-library.info/content/tamriel-timeline for a rough estimate on what could be included in the game in terms of possible cities and such in the 2nd Era.
Why wouldn't you be able to enter the building?
Because you're not a Dragonborn and the Greybeards would just tell you politely to leave (which in turn would probably shatter your eardrums, make your blood boil and turn your bones to dust because ordinary mortals can't withstand the Voice of the Greybeards)
