Retaining wall help!

I attached a photo of the side of my house. I recently purchased it as a foreclosure. My fiancée parks in the garage and I park on the one car concrete flat that ends with the railroad tie in the picture. I would like to build 2 retaining walls. One to sort of match my neighbors white one on the right, and one in front of the A/C unit, all the way across.
Questions:
I was thinking poured concrete but would like the 2 to match so block maybe?
Is it hard to add steps?
The side against the house, can I attach the wall? Is this recommended? There's a door on the comer of that side I would like to use. I would like a wall all the way to the fence. Would I need to make a corner and bring it forward? I want to make more parking space between the 2 walls. I know I would need a dry well type drain in a trench for the front one. I'd like to start the back one soon. My fathers father was a brick layer and owned a construction company so my dad knows enough. But I like to have a beginning knowledge. I've used the site before but it's my first post. Any help appreciated!