I like your idea of painting it grey. I also think a shade of navy would be beautiful. I don't think you should put a terrace, or did you mean trellis (?), between the two porches. I'd opt for a narrow evergreen. A teddy bear magnolia would be lovely. Plus is gives the neighbors some privacy. I'd change out the doors for something in a medium wood tone. It'd warm up the grey and tie in the roof.

Sorry, a light brown / orange roof like this doesn't work with gray unless it is very ably chosen. You can go very modern with a deep charcoal tone - but even then it wants to be warm like kendall charcoal. If you are in a place that gets hot in summer, you may not like the deep shade impacts on your cooling bills or how long the paint tone lasts.

You can more easily do a midtone warm gray that has a camoflauge undertone ... but it still needs to be lighter than the roof for a traditional house form like this. Test something like http://www.benjaminmoore.com/en-us/paint-color/indianriver

It will work with the roof, especially if you take that luscious trim in a creamy off white tone that picks up the warmth of the roof.

If you want a modern result that will work with the brown roof, try navy. Use a teal navy so it doesn't go off black - test bm newburg green http://www.benjaminmoore.com/en-us/paint-color/newburggreen

Crisp white trim, bright red-orange painted doors - now you have a wowsa house.

I think the landscaping is pretty good - don't tear out the tree between the porches . . it is just starting to be the right size. Do get some evergreen flowering shrubs for in front of the porches . . and flowering groundcover in front of those .. ..

Contemporary Michigan Farmhouse · More Info

I think your grey color and white trim would work with a old or new roof.

Have two Houzz windows open - the dilemma and another one where you're searching. Left click on the photo; right click on the description at the top of your screen, use "copy" from the dropdown. Go back to the dilemma page, left click "Houzz Photo"; left click in the blank and your description will appear so paste it and then the photo will show up (be sure to confirm it is the one you intended) then click the submit button