I'm not feeling the grey. I think you would be better in the beige/taupe family.

How about cedar shakes? Natural wood might blend better than a solid plastic color.

I don't think gray is a good option. The only one you showed I would consider is the second to last option as it reads more brown (and purple) on my laptop.

What about a green like this spruce? The brown and green mimic the colors one finds in nature which is always a good way to go.

I think white or light beige are your best options. Next time you need to re-stain the porch, use a deeper expresso brown so it's not so red. Landscaping will go a long way toward making the house more inviting, and the foliage will look good against the lighter house color.

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This was a green option we also liked. I’m so afraid white/beige will be boring but I guess landscaping would help with that too.

A white House is classic, and the landscaping can transform the look by adding color, height, and textures.

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I don't think gray works well with that color of roof.

How about a dark blue (but not too gray of a blue)? Something closer to this first photo than the second in color. But I thought the second one was a good shot of a small house with a prominent brown roof and blue siding.

A nice color for a red/brown roof is sage green. Look at colors similar to Benjamin Moore Saybrook Sage...with white trim.

I'd save a bit more money and have the front half of the roof replaced to match your chosen siding color, and have the roof extended across the gable.

Consider removing the deck, or if you use it, move to the right side of the door so it's not blocking the larger window.

Sage green or dark blue would be my choices.

One thing that I should have mentioned is that the neighbor directly to our right has a dark sage house, so I'm trying not to make it look too cookie-cutter.

I like this blue.