Mad Girl is ready to get inked

I've wanted a tattoo since I was about 15. I remember the first one I was going to get. It was a rainbow around my bellybutton with the word imagine written underneath. I'm glad I didn't go for that one when I was 18. In fact, I held off for two big reasons: money and the fact that I knew I would become addicted. It's no secret that I like tattooed boys. Also, most of my friends have tattoos. I was laying in bed the other night thinking that now was the time. I have a few tattoos in mind that I plan to get over the next few years. The big one is my pin up girl, but I'm going to start small with some cherries:

I know it's simple, but I've always had this thing for cherries. It's something I will be able to live with for the rest of my life and maybe expand into a bigger design (I'd love to get a sleeve). I'm just not sure where to get it. I was thinking that since cherries are sexy and the inside of my thigh is sexy that I should get it there. I also like the idea of getting it on my upper arm on just inside the elbow crook. I worry that the elbow crook might be a little too unprofessional for my line of work though. What are your thoughts?

I want to start with the cherry and go to a really good artist. If I like them they will do my pin-up girl:

I'm thinking about putting her on my thigh. I'm going to change her wardrobe up a bit though. Red bow in hair, dark brown hair, blue sweater, black skirt and stockings and red shoes. She's going to be reading a copy of On The Road. This image has always stuck with me. It's the perfect girl for my first tattoo. My friend has two awesome pin-up girls and I want them to be like hers. They are works of art and very sexy. I'm thinking about going to either Hannah or Kit at Deluxe tattoo, but will take suggestions on other good Chicago tattoo artists.

I have a few other tattoos in mind. I want to get a compass rose between my shoulder blades. This is one is for the traveler in me. I was thinking that instead of directions I can get the names of important people in my life or something like that...not quite sure yet.

The one other things that I'm going to get is a tattoo with my sister. She already has a few and I think it would be neat for each of us to get sister in Polish (which is sisostrzany) tattooed somewhere.

So there is my short term ink plan, what do you think? I'd love suggestions, ideas and tips from those of you in the know.