I have listed my three main challenging test cases below. I didn't have any of the structural analysis tools but I went ahead and modeled the test cases so that it's accessible from BIM360 [linked at very end of document]. It's called 8.5.B Structural Analysis Test Case in my main BIM360 folder.
Test case 1 [cantilevered roof]:
Dead load 0.03kips / sqft
Beam span is 66 ft at longest between the two columns that are straight
10x49 columns, horizontal beam is 14x30, and edge and beam systems are 12x26.
Test case 2 [outdoor terrace]:
Live load is 0.08 kips/sf which is 80 pounds per square foot (seems reasonable for people)
Dead load is 0.03 kips/sf
Columns are 10x33 while all beams are 12x26. The longest span is about 30 ft so it's not as scary as the previous test case but the load is larger.
Test case 3 [cantilevered south side roof]:
For this one, I tried to use a line load to better understand how the load is distributed. I couldn't put a hosted floor on here because the structure of the roof would be different from the floor and I thought it'd be better to model the load in this scenario. I put a line load of 0.1kips/sf to take into account all of the additional weight on both sides of the roof as it sticks out quite a lot. This one is the most scary scenario as I know I probably should put a column in the middle. It would just make my space layout more complicated so I haven't done so already. The beam span is 80 ft and the beam sizes are 12x26