i agree. once you start changing rooflines you quickly get into 'ought to have bought a different house' territory.

distract, rather than enhance. painting it all one color will make it less interesting than your pretty yard. draw the eye down rather than up. maybe some low growing bushes along the lattice under the deck to soften that. creeping phlox along your stone wall will be really pretty in spring as it hangs down.

Thank you for that suggestion. Here are a few more views I meant to include in the original post.

Yes, just too outlined. i think one color will help.

interesting, from the back the 'saltbox' roofline shines through, its the offset nature of the rear addition that makes it awkward from the front.

thats good, you only need to "work on" your front view not all the way around.

A wrap around porch will add wonders.