Cutting through Shed style roof
From a distance view the project in the first photo appears feasible. There are many factors at play here including:


Whether you even need the shed roof at all and could simply fully remove it.
What may be inside the wall area already including wiring or plumbing vent.
Locations of existing studs in the wall and how framing has to change to accommodate the window.
Restoration of the house siding in area where roof is removed.
How to properly flash the window so that rain does not get into the wall.
Opening the shed roof to re-frame one end may result in need to re-shingle it.


Due to the nature of the questions you asked, including the question of what tools would be required, I would suggest that you at least get a couple of contractors to give you some bids on what they think it would take to complete this project. Being on site to see first hand they can give you a lot better idea of what is needed overall than we can from several photos. Even if you decide to do the work yourself the consultations will put you way forward in the process.