Project "Curb Appeal", deciding on Window Colours

So it came down to two colours for our windows. Light (Sandlewood) vs. Dark (Sable). Because it was down to just two, I asked Ken if he could e-mail me some photos of the two colours on windows that they had done, to help me determine which one would be best for us. First up, Sandlewood, which was the lighter colour I was debating. It is beautiful, and classic - But it is kind of light. And for the extra expense of colour, well, I don't want it to read white.

Then there is Sable, the darker colour. And I kind of fell for it.
Honestly, I don't think we could have gone wrong with either. But Aubrey really loved the dark, Ken was confident it was the right choice, and so I signed off on Sable as our colour.

By going with the darker windows, it means we'll be painting the vinyl siding a lighter shade. I used the Sandlewood colour as the siding colour against the Sable windows. But we'll find a Benjamin Moore paint that will go nicely with the new windows.

 I'm getting conflicting information on how dark I can go with painting the vinyl siding, so I'm hoping to get some expert advice soon. And on the topic of painting the siding, I think we may do the back as well. I think painting the white will make it seem less like the back portion of our house was an addition, and make it blend in nicely. (Ok, I haven't convinced Aubrey on this stage of the project so this is still up in the air)

We're going to be hiring for the job of painting the front of the house, but to save money I would paint the back myself.

If you have a painter recommendation, I'd love to know!