This is a case where hiring a designer is money well spent. I know when I work on a project like this I'll do a full 3D computer model of the house and the proposed modifications so we're all on the same page. I don't know what part of the country you're in but you may want to turn to the Google to find someone local (I wouldn't use a random online design house because I'd lean towards someone who 1) can come out and physically measure and 2) is familiar with not just local snow loads but the foibles of your local inspectors)

You have a tough one. Just glancing at it, I can say while you may be able to extend the roof on the right and return it back at the gable, it's going to be visually very heavy. Definitely worth a chat with a local designer or independent architect.

Thank you Marcinde. You are probably correct in the route I need to go. I live in the Lexington, Ky. area and have no idea of a good design team but will certainly try to find one.

AnnCarolyn

Hi AnnCarolyn - it has been a while since you posted this, but were you successful in finding a designer who was able to work with your roof lines? We have a similar problem and have had multiple designers/contractors/architects look at it but they won't even call us back. I'm beginning to wonder if it's impossible....