I would paint the siding a medium taupe, but I'm in Maine without a paint deck so cannot give you a name or number. I'd keep the shutters on the small windows and remove them on the big window. I'd go two shades darker than the siding on the shutters, or maybe a medium-dark green.

The first thing I would say is when you are driving down the driveway or road (where ever you are before you get to see your house) what colour would make you the happiest? It's your family home, when you see it you should smile and your heart should swell and the colour will impact that emotion... barring that...

Too bad about the fire place going... I love the character it brings... I think it looks bad in this picture (granted pictures are deceiving) because of the colour of the house. I would like to see the colour of your windows (the actual window itself) repeated on your fascia and deck spindles posts etc with a cream colour (maybe something like Sherwin Williams westhighland white or ben moore flurry - basically a heavy cream) on your window trim (lose the shutters and increase the frame size) and ceiling of your deck and maybe even your deck itself although that would get dirty quick but would totally brighten up your entrance. Use a stone grey like SW keystone grey on the body...(unless that colour looks awful with the stonework then brown up the siding colour and you may have to make it a bit more golden depending on the tone of your stone) and of course your favourite colour on your front door! It would create a really soft look in that setting and should make your stonework blend... I don't think the colours are really going to determine the maintenance of the house though in any significant way...

Maybe it's just me, but I think this house is quite charming the way it is. Perhaps you can change up the color scheme to other neutral tones to give it a bit of update.

Replace a NEW roof on a place you're in only occasionally? Leave it and use the money you save to pay someone else to do the upkeep drudgery.

Why is the chimney coming down? If there is a structural problem, fine, but if you just don't make fires, decorate the empty fireplace and be done: come the day you decide to sell it, a working fireplace and beautiful stone chimney will be major selling points.

Wood shutters, highly classy. Vinyl shutters, no painting, just cleaning.

And before you commit to anything, get up there and eyeball the place in person! One guy's gray is another guy's brown. The cream may be yellow to your eyes.

Thank you for all the input. I really appreciate it. We have had this place 5 years and we were lucky to postpone a new roof until now. The shingles were starting to fall off and it was a mess. As for the chimney, you all seem to like it so I'll get over it. I am getting used to the stone. The problem is it's kind of coming down on its own. Those stones will hurt if they hit me! We will check it out next month and see if anything else is loose. I love the idea of lighter more neutral color. Maybe if I lighten it up we will see more than just roof top driving up the hill. We bought the house for the view. It's a lot different than Florida. There's a lot of mowing to do when we get there so that's why I'd like to keep things low maintenance.

Gorgeous!

Ah, now things make more sense! A chimney lying in wait to drop a stone on your head cannot be tolerated in that state.
What about a metal roof? They last for ages,
Good luck!