I am about to buy an English Tudor Revival-style duplex that has two bedrooms in each unit. I'll be living in one unit with my brother. There is a potential for four cars hogging up what is currently a single-car driveway. (Actually, if we are getting worse case scenario, I guess there can potentially be up to about 8 cars in the drive, but I'm not looking at worse case.)

I'm looking for help on either gathering ideas or actually designing an attractive driveway/parking plan in my small lot for four cars to regularly park and pull out without turning the whole place into an overbearing concrete parking lot.

I was originally thinking of adding a circular drive in front but I don't think I have the room in my skinny lot.

Here is the current property survey:

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You can view larger by clicking on the picture and clicking "All Sizes".

It doesn't note any planting, so here are exterior photos for a further frame of reference:

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I'm not sure if I'm supposed to lay out all my problems on the table or if it is better if I just focus on solving one problem? The above is my most pressing concern, but just in the interest of disclosure, here is more about my wants:

1. Style-wise, I like a semi-formal look to a landscape and am particularly attracted to cobblestone and pavers for the driving surface.

2. I need a dog friendly backyard. I will have 2 dogs and the tenant has 1 dog. I don't need a huge blank patch of grass, but a nice little bit to run around in the backyard would be nice.

3. Grass strip aside, I'm otherwise partial to an overgrown abundance of plants, much like the cottage garden look. Except a little bit more structure to the planting. Again, not to be contradictory, but I prefer semi-formal cottage garden. ;)

4. Another problem: I've found that people just don't realize that there are two front entrances to two different duplexes for some reason. Look at the pictures. I think it is because both doors are hidden away. People just don't see them when they are walking up. So when they find one, they think they have found the only one. Can this be solved in some manor with the walkway to the doors?

5. This is detering off into architecture, but I'm not a huge fan of the current porch/stairs in the back. I'd love ideas on how to improve this, perhaps by making them more outdoor spaces than stoops? I'm particularly disgruntled by how the stairs eat away at the exterior. I don't think it is attractive. But perhaps the solution isn't really reconfiguring the porches and stairs? Perhaps a better solution is hiding the unattractiveness with landscaping?

6. I'd prefer the backyard to be a place for semi-private relaxing and entertaining to be done. I'm imagining chairs, trees, shade, grass, and, unavoidably to the side, a parking area. I'm going to remove the silly chain-link fence next to the current driveway that splits up the backyard and am thinking of putting one of those automatic gates on the driveway to help keep the dogs in and strangers out.

7. I want to add a backyard shed for the various bits of equipment, but I am otherwise not going to be adding a garage anytime in the near future.

Hopefully someone can help me out with a direction to go with this. I feel comfortable with interior design but I am completely out of my element when it comes to landscape design.