I think white trim would look perfect and provide a very nice contrast and even help tie the colors in together. You have to remember any semi-transparent stain on a RED cedar shingle will still show the red through quite a bit. Also I doubt very much that the stain separated at all as semi-transparent stains really do not have much to separate.

Thanks so much NoSoccermom -- your interest in my project is soooo helpful. By chance, just today, my neighbor stopped by who is an engineer (the worst) but worked as a professional painter and general contractor as he worked his way thru college. I've been dying to call him about all my projects but today worked out perfectly. He's finishing his basement and asked my ideas about that and I had a chance to walk him thru the almost finished Dining Room (he was impressed) and then we talked about the crazy Living Room with paneling/shake/beams/etc. He loved all your ideas about keeping the shake. He offered to help me remove the paneling and fix the walls OR apply NEW drywall if that is what I want. Cleverly ... he mentioned ... if you really want to accent the shake like it was "intentional" minimize or remove the other materials. Lastly .... he advised on my ceiling which he's done before. After a lengthy discussion ... I have to basically stipple these tiles (brush-fill all the holes and groves) then roll with a nappy roller. I can do that. I can recruit my Hubby to help. In return, I've offered to help finish his basement when it comes to painting as I meet his level of excellence. LOL. I'm in good shape for now. I'll post pictures of the entire room before / during / and after. Also, I feel obliged to send you flowers or something in appreciation because you've really changed and IMPROVED what I was going to do. Thanks soooo much. And thanks to GW Home Decorators. You folks rock! :)

If the shingles are on lath that will have to be removed and the roof sheathed in plywood,you mean need to have the soffits redone with vents, so while Architectural Shingles may be cheaper your labor and other material costs will be higher due to plywood install. I would suggest going with an Owens Corning or GAF shingle and just as important as getting bids is checking references for the roofing contractors

If you can get a oil based stain that might be your best bet. But my house is cedar shake and I believe it has always been painted. The paint holds up well. I really like the green windows. I think you can highlight some of the trim with two shades of a brown gray like this house. The siding is a Cabot Stain, Bark color and the trim is a SW paint, semi-gloss, color not known. I really don't like the color of the front door. I think it would look better in the trim color on the sidelights and green on the door. I would do the foundation and the garage door the trim color as well.