I think you would have to raise the roof of the lower wing. It would be expensive for a little return.

Are you trying to change/improve how the flow works inside, or are you trying to improve the exterior appearance? Anything is possible given enough money, but your existing roof is not identical to the roof in your inspiration pic, so this would not be easy. As houssaon says, high cost, low return.

If you want suggestions on how to improve your curb appeal without expensive modifications to the house, people will be able to make suggestions along those lines. Tell us where you are so we know what kind of plants would do well. You have almost no landscaping presently, so that would be where I would start.

Lemons not worth the squeeze. You need to rip the lower roof off completely and reframe it for what you are looking to do. Not cheap.

This would be a hugely expensive undertaking involving strcutural roofline changes and more. To differentiate between the driveway and house, you could instead build a pergola (there are also pergola kits available)and possible planter, which wouldn't involve structural changes you're thinking about and give you a porch effect. Use the money you save to skim coat the driveway and add flagstone to porch and new area to define it with a kind of patio entry.

Additionally, spend the budget on landscaping that lawn with a front garden or a tree with a deep bed around it for perennials--something to enhance the house instead of a boring lawn. Your place has a lot of potential for exterior improvements without going overboard and messing with the roofline.

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A front pergola. You could get one built just for the left side, possibly with a planter in front of it and over a flagstone porch across the front of your house. I could be gorgeous.

New walkway something like this from driveway to front door.

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There's so much you could do with landscaping instead of spending massively on huge structural changes. Also consider that you are parking two big vehicles in your driveway, which is in such poor shape. Concentrate on landscaping the lawn part of the yard to draw attntion there. You can create a pretty seating area/porch with small pergola, flagstone, porch, planter. Get a professional landscape designer to come up with plans with the thousands you'll save.

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Beautiful landscaping in front of small house. A deep garden bed on the right would give you something to look at from a smaller scale porch instead of the car and truck parked on the left.

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Cute small house, blue door with charming landscaping.

Even if the roof could be easily and economical extended to the left, you’d have a porch sitting up against the concrete driveway. Not a good look, or a pleasant place to sit. Instead, a lovely garden on the right side of the house would be a big step toward improving curb appeal. It would also draw the eye away from vehicles parked out front. An out of sight place for the dumpster would also help. It’s a cute house!

I edited the post I left out we are removing the driveway. Currently, we are doing a whole home remodel inside and before i paid the Architect we were looking for ideas. The kitchen is being moved changing the flow of the house. Before we had the brickwork done to fill in the old garage door we were just brainstorming. If there was a simple way to extend the porch. As someone mentioned completely reframing the lower roof isn't worth all the money it would cost. But we are leaning toward possibly doing a pergola as someone mentioned above.