I pretty much agree with everything BatElite already stated. Except the first one because I really don't know my medieval tavern architecture that well. Good critiques regardless.
I think your tavern sign is looking a little weird. The perspective seems strange compared to the entire thing. It's facing the wrong way and seems to be going to adifferent vanishing point compared to the building. The shadows cast by the dormers still seem very extreme and very dark.
Another thing, will you add more texture or variation to the roof tiles? I think it would help having leaves, cracks, wooden plank repairs, slightly different coloured tiles, etc to break up the simplicity and repetition.