Converting a flat roof to a gable roof?? New at this!

I have a small building that I purchased and am rehabbing. I have never done this before, and the projects are going slowly. Half of my house has a flat roof that I would like to convert to a pitched roof (for a bedroom/bath). Any suggestions on how I can add this to the exixting pitched roof?
The roof that is to the front of the house is not quite tall enough for a taller person to stand up, so the addition would have to be higher than the existing one. My son does framing, but he is a bit confused as to how to approach this problem.

 

I would suggest you start by getting some estimates from a couple of contractors. They will point out things you might never consider, and they are on site as we aren't. At the least, you will get a lot of free advise. At the best, you might find someone who can put up the shell for you. Getting the design correct and the the shell up are projects where the pros do best. Then the diy'ers can get started.

Since you will be changing the structure of the home, you will probably need to pull a permit, but that varies from location to location, but check.

See what you get for estimates and what they say about the project, and let us know.

HH
Bud