I may be wrong, but I didn’t get the impression that the clock striking was for 8 o’clock. I was assuming that school started around 8, and Emma was talking to Henry before the school bell. Not being from Maine I’m not sure what time is sunrise, but the look of the town looked like it was just around sunrise to me.
I think Jefferson sounds like a whole new series, an almost “Time Tunnel” or “Quantum Leap”. He drops into Emma’s hat, but none of the doors have any clues to their worlds. So Jefferson in order to get his daughter and return to FTL must go through chance doors; overcome adventures and mysteries and try to gain clues on how he will be able to get his daughter and return home.
If I were Emma, I would move into Jefferson’s mansion. I would wager that Regina probably can’t use the mirrors in there.