Congratulations on your new home! A new house always brings with it particular concerns and needs and sometimes all those things can seem overwhelming. Don't feel compelled to do everything at once. You know, kind of take it slowly. But it sure sounds as if the driveway should be tackled first, especially with the possibility of car damage --- that could be very expensive!

Is that a shared driveway entrance? It doesn't appear as if you're on a corner. A few photos taken from different angles would more clearly show the driveway and its relationship to the street.

Molie

To answer your question, you should do the driveway first!

That is because you said - We have to do the driveway ASAP because there is a curb there that I have hit a few times coming in to the driveway :(

What a cool place, congrats :)

thanks for all the feedback, folks!! good advice, I think we will start with the driveway, just keep it pretty simple (though may do brick...) and just widen a bit... less stressful that way :)

and that is actually a shared alleyway that runs behind the houses, the front of the house is actually on a corner

I am an old home owner, and here is what you need to know. It is hard to talk to driveway contractors. You may not speak their language, neither literally nor figuratively. If you do not tell them exactly how to change something, they will repave it Exactly the way it is, with it's flaws. You need to articulate to them how you want it to be different. You need to be there the morning they show up and remind them how it should be different when it is done from what it looks like in the morning. This is true about a lot of things you have people come and do on your house. If you are not monitoring them, you might miss something and they go away, and it is hard to get them to return your call if they think they are finished. Ask a friend or relative who has done construction projects before for advice.

People looking at the photo don't know if your driveway is off someone else's property and driveway (shared) or if this is a back street or if it all belongs to you. The part that goes to the garage looks unconventional, and hard to manage except with the teeniest of cars.

Thanks for clearing up your situation, Kriscoop.

Since what we see on the left is a "shared alleyway that runs behind the houses", I think that your new driveway needs a more defined turn-around area on the right side. This will allow you to back out of the garage and turn the car around before driving onto the main road. (I'm assuming that the car shown in the corner of the photo is on the main road.)

You said you wanted a brick drive --- are you doing it yourself or hiring a contractor? I ask because there is a sharp drop a few feet out from the garage. It looks as if this whole area will need to be regraded to a more gentle slope and that a new surface will have to go under the bricks.