What are his goals? Is he moving up for any other reason than you nagging him? If he is comfortable at .5/1 and is making enough money at it to make it worth while for him he doesn't need to move up. Penis size and the limits you play at are rarely linked.

Table selection is important at every limit. There are tight tables and loose tables and finding the table that matches your play is always important.

Have you shown him Poker Ace in action to let him see what he is missing? I think if he saw it in action he would be more likely to get it.