So, apparently, since he did not have a ladder tall enough and someone to help him get it up there, he just hung out the 3rd story window, and scraped and painted the soffits with an extension pole and a roller. I give him an A+ on ingenuity.
He's home again working on some more window trim and soffit painting... pictures will filter in through the weekend (sorry about the iphone quality photos right now, I'll have some nice high-resolution ones whenever I get home early enough that there is still some sunlight out).
We decided to go with all black trim around the windows, and for the soffits, with a golden-yellow for the front door. Go bold, or go home I say!! (no really... go home!)
some before (left) and after (right) of the windows ... I think they look SOOO much better! (this is also just a temporary fix until our brand new windows come in, then we will be recapping all of the windows in black).
We are going to try to salvage the old copper gutters... but at the moment, it's not looking very promising... I'm pretty bummed about that really, but in the meantime, here is a before, and "after" (photoshop) of the front of the house. The awnings will be taken down next spring, but in the meantime, we'll be painting them a gray, to blend in a bit more than the faded and striped green they currently are.