lol......... (& congrats)
really can't tell much from the pics,
but it does look like that chimney might need some work-
& "Southish facing eave:" left over antenna brackets?
Do you know how many layers are on it?
Do you know what the sheathing is? (probably see the underside from the attic.
Doesn't look like there's any-you might want to have some ridge vent installed-
& What's under the siding?
Funky little house, though-
I like the front (I think it's) stucco area-
Good luck with it...........
if you ever have any (exterior) trade-type questions feel free to ask~
