What about something along these lines...
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This is the garage that Dski and I built for our principal residence. It's a 24' x 36' footprint. The upstairs is unfinished and used for storage, but I have often stood up there, looked around, and thought about how cool it could be as living space.
The opposite side of the roof is the normal gambrel; no shed dormer. Perhaps we take this design, add the shed dormer to the other side and stretch the footprint to 28' x 42'.
Because of the site layout, I have to have a side loader garage. I would flip the doors to the right side and put all the living space upstairs. The hay loft door in the pic would become a wall of windows. Since all the living space is upstairs, the ground floor is one large garage and shop area.
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OK....start kickin'
