Starting with Leica? - literally

You should start with Leica. There is no need to work your way up, some people think Leica is the best camera, or it is a hard camera to use, all well. You buy it you will learn to use it. Or you wont and your wife will say I told you so. If you like Leica use Leica, learn Leica, don't learn other types or brands that you do not care for. You don't want to be professional photographer, you want to have fun taking pictures, so get the camera that you can have fun with. If your pictures look "bad," all well they are your pictures to make better. I was just in DC and went to the Leica store, if I could afford it, I would have a Leica M. I would learn how to use it, it feels great, and though I only got to use it for a few minutes, I quickly felt comfortable with it. Manual focusing is fun and easy, and so is the Leica M.

Also just general information, the Leica store is fantastic, the staff is great they let you look at any camera, they actually seem really eager to shove cameras in your hands even of you are not that interested, in that particular model. I was talking with the sales person, it was an Asian girl who is an art major in the area, she pulled out almost every model they had and went over them in detail. They have some nice brochures also. And also they do not have any used equipment.

Its your money, its your hobby, its your passion, do what you want. I bet you learn to take some great pictures quickly.