Hi there. My 1985 Victorian home here in Maine also came with a 35ft x 25ft two-story carriage house. Bonus!

Our goal is to park two cars in the first floor and keep the second floor as a workshop for now, and maybe an inlaw apartment in the distant future.

It currently needs a fairly intense renovation including a new slab/foundation and all 4x vertical walls down to the studs. Also, it is positioned awkwardly close and tucked behind the main house. Driving in and parking 2 cars will be difficult. Attached is a quick rendering of the current layout, roughly to scale. The rest of the driveway remains very tight against the side of the house with no extra room on either side. I included 2 Volvo station wagons to help visualize how cars might park.

I'm wondering if it's possible to rotate the position 90 degrees and install the garage door(s) on the wide-side, instead of what is currently the front, narrow side. That would allow much more maneuvering room between Carriage and Main House, and allow both cars to just pull straight in.

What do you think? In your opinion, is the current position/layout livable? Is the cost to reposition too great to make it worth while? I'm not really sure where to start.