Table selection depends on the site you play on. Party shows number of players and average pot so I figure the higher the pot the looser the table and choose accordingly.

He wants to make a living playing on-line poker and doesn't understand position or table selection or how to maximize the available tools out there? It didn't really sound like .5/1 wasn't still testing his skills. One profitable month doesn't mean you are crushing a limit. Tell him to move up when he can sustain 2 BB/100 for 50k or 100k hands, if he doesn't have the patience for that don't lend him money when he goes broke moving up too fast or with too little bank roll.