Working on Curb Appeal - Exterior Paint Colors

Outdoor projects tend to be a little slow going around here, but we've been chipping away at it. Last summer we focused on the back side of the house by replacing our old rotted deck and also building a large garden shed. Er, well, Jesse built it. I entertained B. This year, our main goal is to get the house painted and possibly do some minor remodeling work to the front porch area.

I was absolutely dreading painting the house, mainly because I couldn't figure out what colors we should go with. Our roof is an odd terracotta orange brown color so I figured we'd end up painting it white, which is just kinda...meh. I was also dreading the task because I figured it would drag on all summer.

But then, a few days ago, I came across this beautiful image via Houzz that inspired me in terms of paint colors.

Farmhouse Exterior by Bristol Architects & Building Designers Joan Heaton Architects

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Farmhouse Exterior by Bristol Architects & Building Designers Joan Heaton Architects

Isn't that gorgeous?  Our house is a Plain Jane ranch, but I think we could steal the color combo.

I also love this front door. Ours would look great like this; I'd need to strip off the paint first, but it's do-able!

Source: David Erwin, Crestviewdoors.com

So, now that I have general paint colors figured out, I'm actually looking forward to getting the house painted because...drumroll please....I don't have to do it!!! Yep. That's right. We are hiring a local contractor to paint our house. I know, I know. As my friend Rebecca said, "it completely goes against (our) DIY code!" Here's how the logic works in my mind; we can spend all summer agonizing, laboring and probably arguing over a half-painted house or we can invest in someone else and therefore invest in more family fun time. What do you think? Good logic?

Hiring someone to paint is a big purchase for us. It's a big deal, and I want to make sure we get it right so I'm debating a little on exactly which shade of gray to go with.  Here are a few images of our exterior. Oh boy, our house needs some some curb appeal in a bad way! I'm a little embarrassed by the current state, but we are moving in the direction and in a few weeks it will look lovely. Fingers crossed.

Here are the colors I'm considering:
Left of window: Sherwin Williams, Gray Clouds
Right of Window: Sherwin Williams, Silver Spoon
Under Window: Sherwin Williams, TinsmithThe colors are all very similar and I'm sure any of them would look fine; but I'm leaning towards Tinsmith because I think it would look the most like the Vermont Farmhouse. Jesse likes the darker Gray Clouds color. What do you think?