Is there a back yard? That's what I would fence in for the dog and then remove the chain link fence in front. If replacing the roof maybe consider removing the portico. I would paint the wood the same color as the bricks with chocolate trim

I was hoping to change the color to something more modern while keeping the natural brick color as an accent if possible. Since the roof is going we pretty much have a clean slate.
As for the fence, that was exactly my thought, but the hubby wants the dog to be “out front” with us when we are doing yard work or whatever.
I’m also wondering if there is just a better style for a portico that would highlight the main entry door? Not sure if the photo attached here shows it a little better, but with the sloping roof I don’t know how to make the door stand out, or even if it should.

Not a pro. Jck910 gave some excellent suggestions. IMO, your entrance should stand out in order to draw your guests in; to achieve that, I suggest painting your door a welcoming color of your choice.

As far as the go for something more modern looking matching the style of your home. Have the gate about halfway between the house and the corner and bring the walk from the front door to the gate. Paint the front door a more welcoming color. Leave the mudroom room same color as the trim.

I like that idea for the fence, thank you! Really like the gray shingle too.

I think they did a good job on the portico, which covers both entrances. Once you get your new doors in, they will be much more inviting than the current ones. Maybe the same for the mudroom door or a solid one. I like your garage door idea, too.

I would look at charcoal roofs. I would paint the siding close to the color of your brick. Change the fence, at least in the front and the side by the garage.

A cattle fence would look modern and would be open enough so your property is visible.

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BM Thunder might work:

The portico is really functional and I like how it covers both doors, but...it isn't quite right. Fixing the slope to match the main roof before the new roof goes on would be a good thing...or perhaps going totally flat. Hmm.

Put the fence in the backyard and tie out the dog when you want him with you in the front. :)

Uhhhh...don't tie a dog up, ever.

OMG, I love the mock up with the roof in charcoal & the doors I want! That cattle fence style looks really good, I’ll have to decide how to apply it, jck910 had the idea to shorten the fence length & the other option that I had not realized is that we can have a tie out there for him since the whole front yard is a straight line (doesn’t work in our current house). That black fence though :)
I was thinking the same thing with the portico Fori, like a straight across form, I just can’t picture the material or colors or anything.

I like the cattle fence too. It's a good style for the house. You can always add it later if you decide you need it.

I use a dog run out of my back door. It works fine.