GeneDavis

Select the two end walls, at right and left side of building.  In ROOF tab of wall dialog, change the pitch to something higher.  If it is for example, 3:12, jack it up to 6:12.  Autoroof should then generate the roof with a ridge parallel to the front and rear walls.
 
Now play with all these pitches until you get what you want.

Nope.  Walls are rectilinear.  In your case I would do the wall as a wall, to the point of the bottom beginning of the lean-out, and only use a solid for the angled-out segment.  Dashed CAD lines in a plan view and annotations with CAD details for the rest.

I am back because I think some more needs to be said about not this problem caused by somehow wall def getting improperly spec'd, but to comment on @Cadwork22Michael's larger problem, that of not knowing the most elemental basics of Chief.
 
I downloaded and opened to explore the Barndo plan, and it is a very simple three bay two story thing with one single shed roof.  But how it got built is kind of a mystery, and I did not want to waste time trying to imagine the sequence of walls, floors, etc.  The plan, simply, is a huge mess of bad practice.
 
In just a couple of minutes, I drew the a floor plan of something with the same footprint arrangement, drew interior walls to make it three bays, just let it all auto-roof from the OOB setup defaults, added a second floor accepting the same exterior perimeter, drew railing walls over the lower floor walls to create the balcony rooms, then specified the center room as "open below."  All it then took to get the roof about right was editing the exterior walls for roof definition (slope, hip wall, gable wall, high shed/gable) and it autoroofed as wanted.  Here is a glasshouse view of my quick build.  One single roof plane, three rooms floor 1, two lofts with railings on floor 2, center bay open below.
 

 
 
Michael got an answer here as to how to get the loft floors to generate, but he got no real direction about how to correctly build this very basic arrangement of rooms with the roof over he wants.  Until he takes the time to learn, either by video and study and practice or zoom sessions with pros, he is still going to flounder.  Posting badly-built models here and getting quick fixes for single-issue problems ain't a good learning process.

Select the window after creating the custom muntin array.  Go to Lites.  Change muntin width to something else.  Worked for me.
 
As for your connection issue, I've no clue.  Try dividing the arc into three segments, then making each side polyline a side arc and a vertical.  The center segment arc is all by itself.  Then block the three p'lines and see if the verts join to the arcs OK.

Almost anything is possible with solids.  Try it.

You can set that in General Framing Defaults for floor framing.  There is presently no way to set rims for decks differently (width and material type) from floor framing, so unless you want to take the time to edit all deck rims in your final config to 1-1/2" P.T. lumber,  you have to frame in this sequence, if floors (not decks) get engineered lumber rims.
 
Set the floor frame rims to be 1-1/2" and P.T. lumber in the defaults, build deck framing, but do not build floor framing until after all decks are settled for size, elevation, etc.  Now with decks framed, lock their framing by turning off autoframe for decks, locking their layers,  and only then change the framing defaults back  to however wanted for floor framing.  You can now build floor framing.

There is SO much you can learn about using Chief on YouTube.
 
I searched roof purlins chief architect.  
 
 
https://www.youtube.com/watch?v=rXphFJLHiTM&loop=0
 

Chief has a sample file at their website.  The building is a pole barn with metal roof and sides.
 
The project is titled Post Frame Design and includes the plan file, a .pdf of the layout, and links to How To Design videos.

 

More CAD polylined, color fill, and learn to use the order of draw tools.  Use Chief's Help files to learn.
 
 

Draw a test building in a new file.  Four walls with the out-of-box Siding-6 woodframed walls.  Frame it and look at the 3D framing view.  It'll be studs.
 
Go into Defaults > Framing > Exterior Wall, it should be Siding-6.  Edit it so the framing layer is changed to steel, and the material down below is changed from lumber to steel C.
 
Click OK to change the default.  Your 3D view, if you had things set to autoframe, is now changed to steel.

Click-select any room, or click all that have the same spec for floor sheathing and floor finish.  The structure tab in the room spec dialog that opens has what you want.
 
At the bottom of the panel, floor structure, click edit to open the spec dialog.  Chief out of the box will show two lines, sheathing atop framing, and each line can be selected to activate a structure type (or not).  Note the choices.  Framing.  Detail as insulation.  Air gap.  Or don't check one.
 
The top line, typically subfloor at 3/4" plywood or OSB, gets a no select (no one of the three are checked).
 
The second line, typically framing like sawn lumber, i-joists, open web trusses, whatever, that line is going to be checked as framing, and the floor when framed will be autoframed with that material at the spacing specified elsewhere.
 
Up-page, same panel, there is another box you can edit where floor finish is specified.  Again, you can oreo-cookie up some layers, like for example, engineered t&g wood over a thin foam layer.  Again, you can specify any layer as framing, and you must have done this, as you must have done for the sheathing in the floor structure dialog.
 
Please consider spending maybe 40 hours to watch many of the training videos on Chief's website.  You seem to be playing monte carlo Chief right now.

I don't see a way to get auto dims to pick up the lower wall of your pony wall.  I did a test plan 4-wall building, walls pony with siding-6 upper and 8" concrete wall below, aligned to inside main layer.  Autodim picks up the siding-6, but manual edit to make it pick up the concrete wall was quick and easy.
 
Here is a workaround.  Set the wall display in the pony wall dialog to show lower wall only, then autodim.  The dimensions will pick up the concrete wall.  Go back and change the display and the dims will stick.

Always edit floor heights doing top floor first and go down.  You'll get it once you've done it.
 
Once you've changed the floor structure in all the upstairs rooms (and you've used Match Properties to do so), go to floor 1 and work the ceiling heights using the same Match Properties tool.

We've been down this road with this exact plan.  
 

Uncheck "retain all framing" for those walls, in the structure tab.  You must have checked that box before trying to frame.
 
All frame fine when that is done.

Blocking CAD objects creates a new object, let's call it the "block," and the block can have its layer different from the layer or layers of those elements which were blocked.  Think of those layers as now subverted or made moot.  You now control visibility of the entire grouped blocked thing, the block, by its layer.  
 
You gotta explode it to regain viz control of the elements, which when unblocked, now retain their original layer assignments.

One door, options tab, 2 panels right, two panels left, looks like what you want.

Cannot remember whether X10 had structural member reporting.  Do you see it in the defaults:  Tools > Materials List > Structural Member Reporting?
 
You have to set this up (if it is there in X10) to get framing to report piece counts in your specified lengths. 

It's not that intuitive, but you can set up your file using a framing defaults and wall specs, plus material list to do the "buy list" reporting, and get pieced framing like what one does at build time.  By that I mean mudsills, wall plates, and deck rims modeled and reported in the material list in your specified max lengths.
 
If for example you have set your wall plate max at 16 feet, the count is going to give you, for a 17 foot wall, one 16 foot piece, and one one foot piece, and it is tallying the one foot piece with other shorties from elsewhere in the build, to cut from 16 foot pieces.
 
What Chief does not do, but what a framer does, is cut the 16 footer back to the nearest stud or joist center, so the butt joint falls on a member.  Chief will put the joint wherever 16/0 falls.
 
As others have said here, there is no such way to piece rafters with a bearing line dialog, as there is for floors.  There is no way to specify a max length for fascia or subfascia or ridge members, either.  They will build at full length and report to the material list in lineal feet.

Use solids to make your truss and put it wherever you want.  A floor truss can only be put in a floor envelope.  What you want is a truss as a drop beam, something Chief does not do.
 
If it is not important you see it in 3D (will 3D views be in your con docs?), just do a beam the size of the truss, and label it as TRUSS in your structural plan views.  You can use CAD to show something in section view.

I made a 3D solid to do this.  You can rotate framing in a wall layer that is framing and built with its studs and plates, but you cannot rotate general framing objects.

I've done it making two roofs:  The gable overhang has open soffits, the one starting at the building line does.  Not pretty in plan view, but does the trick in 3D.

I belong to a club of about a thousand members.  At any event or meeting, we all wear our name tag badges around our necks on nice logo (it's a car club) lanyards.  It is a great big group, much larger than my Rotary club meet, which is nametags also.  It is simple courtesy to wear the tags and badges, even though most of us know most all the members.
 
It is a courtesy here to do the same thing.  Your sig which gives very important information relating to software version and hardware on which it runs is essential to knowing how to respond to a question or problem or issue.
 
So be courteous.
 
Attached is a view of a plan with valleys in the roofscape.  I pulled back the planes at one of the valleys, six inches exactly.  I could make a copy of the building right alongside this one, auto roof it, edit the roofs away to leave just two 6" valley planes (the "valley patch"), retexture them as galvanized steel, and then copy and paste this into the roof with the gap valley.
 
So this was a courtesy, and we'd like to see you back sometime, all badged up.

It's a toggle, and you might want to add the three buttons to your toolbar, as most need to swap and change depending on situation, and it's too tedious to make the change going to Edit>Preferences>Marquee Selection . . . 
 
See the attached for all three added to the toolbar:  Contained, Intersected, and Centers.

Solved!  Deleted the window in layout and ran it again, and it's OK and with cornerboards.