Beginner struggling with Cape Cod roof w/shed dormer


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I am planning an addition to the back of our house which will involve removing a good portion of the rear, load-bearing wall.  I spent many hours trying to build the house using HD Architectural and could never get my roof right.  I called tech support and was persuaded to upgrade to Home Designer Pro, in order to have more roof options and flexibility.  I did, made some progress, but now I’m stuck again.

My specific issues are with the roof where the garage meets the house.  The saltbox style garage roof joins the same plane of the roof in the rear of the house, however the software keeps showing the garage taller than the house.  
The entry of the house is two step higher than the garage in reality, so if I knew how to raise the house foundation up out of the ground about 14" that might help with my roof issue - not sure.
Additionally, the upstairs of this cape cod style house has knee walls that are 60” high and ceilings 90” (7’6”) tall.  Anytime I try to mess with those items on the second floor the dormer disappears and I panic and undo to get back what I had.  
The planned addition will be "L" shaped, 10' deep across the entire back of the house with the furthest right side coming out 22'.  The long portion will be a gabled roof and the rest will be a 3/12 pitch lean to type roof.  All that to say, it's imperative that I get the existing roof and dormer right before I can accurately blend the new rooflines into the structure.
I appreciate any advice offered to keep this project moving forward.  
I’m working with 2016 version of HD Pro.  I've attached the file and actual photos of the house.
Thanks, Jeff

2650 Shepard House, Original.plan




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