Honestly? Yes.
I actually wrote into ThisOldHouse, but I know that's a long shot!
What's the worst that could happen? It could fall off the roof while I'm in it and plummet 35 feet to the ground below. uh.... yeah. that's pretty bad!
The hole in the roof is a fully framed in rectangle that is extremely solid and supported. I think it could be built on the ground and then lifted with a crane and "dropped" into place, but that would take some doing and just
might be out of my skill level. (yeah, "might"

). It is accessed by a 3 foot wide staircase, so could also be feasable to build it in place. I have no fear of heights and the roof is relatively flat so it might be possible to build pieces in the bedroom below and carry them up. (I'd invest in a climbing harness for a double safety measure.) I would definately have an engineer come in to specifically check the roof timbers and
make sure that a ton of lumber and windows wouldn't come crashing through!
I know how to correctly build framing for load bearing walls, frame in windows, build / support a balcony and an overhang deck. all of those things combined could make a coupla. Of course all of those things combined could be a disaster! Yes, I am realistic about things. I figure if I wing it and it doesn't work, I have a cool tiny gazebo for my yard. Talk about the world's most expensive dog house!
The plans for some of the oldest homes in the city I currently live in are at the historical society down town. There is a chance that an Italianate coupla is still in those plans somewhere.
My added bonus is an original photo of the house from about 1900, so I know what it is supposed to look like. Most houses like mine have had the staircase to the coupla ripped out to be replaced with a hole in the ceiling. Previous owners built hardwood bead board closets in the rooms that didn't have closets, they are not beautiful, but they are 10 feet tall with a closet space at the bottom and a cabinet at the top.