What do you think of my 'gonna-be-boyfriend'? rate 1-10?

I can't see the picture, but from what you say it seems like you will have some competition. If you think you can snag him though, who cares about the competition? Go for it, and he doesn't seem like he'll have an ego. He may be uber-confident in some areas, but I don't think he'll be a y jerk in general. Seems like a good catch!