Most Helpful Girl
Don't get anything on an area you think you won't be able to hide well. Especially if you're going to be going into some professional.
Your tattoo should reflect who you are and what you want. Opinions are good but at the end of the day, it has to be your decision. The last thing you want is to get a tattoo and reflect on it later as being a mistake you did.
Pain is pain. There is no such at thing as the least pain when it comes to getting a tattoo. It's 10 needles piercing the flesh at once. The thing you need to learn is to keep your mind focused on other things. Over time, the pain will become tolerable.