OKAY,

So...That sure took longer than a week lol I ended up ordering Chappell's "Advanced Timber Framing" book. Right now, the design uses a partial octagon bay with a king's post (entry door is gonna be on the bottom right corner of the octagon in the 2nd image), and a modified, split shed-style roof for the rest. Those are gonna be clerestory windows coming off the octagon bay.

Can anyone lend me their more experience eyes and tell me if there are any obvious structural problems here? This is the wire-frame, I still have to work out the size of the timbers and the joinery: