[Just Peachy.]

Pain from a tattoo is different for every single person. If you have high pain tolerance, it's not likely that you'll sit in there and bawl for two hours. But yeah, it going to hurt. Not going to lie. Best way to describe a tattoo: like a cat scratching on a sun burn. And for the tattoo rubbing off, it is a tattoo so that won't happen quickly. And you can always get touch ups.

As for the design, you could even draw up a really rough copy of what you want and he can draw it better based on that. Doing it in the computers are good too. You have to remember that the tattoo artists are artists. They're going to have ideas, suggestions, etc as to what will look the best. This is particularly helpful when you're clueless in not knowing what you want

Lastly, work. As long as you don't have it visible then you're good. Most jobs require you to wear closed toe shoes anyways. Maybe not most, but a lot. And a lot of places are more accepting now a days. I think as long as it's respectful, and appropriate and not on some weird spot on your body (like your forehead) you're good