[excession]

OK first question... is he interested in poker at all?

Poker is a hard slog - mentally it requires immense discipline and the very unusual ability to realise that the instant result is not to be taken as positive or negative reinforcement of what you are doing.

It really really helps if he is fascinated by the game first and foremost.

It is soul-destroying and much harder than it was to start grinding up the limits purely for cash gain.

If he wants to play then let him learn - just point him in the direction of the linked thread, buy him PokerTracker (or holdem mananger is it's out when he starts) and give him $100 or whatever to play the micros.

You don't need to roll him $1000+ - people who are learning from scratch should be limited by experience and skill level, not bankroll - if he puts in a month or two of solid winning poker at any level he will automatically be rolled to move up anyway.

The two reasons that loads of bright kids round here go bust are inability to mentally cope with downswings (it's the lack of control over them that tilts/demoralizes them) and moving up too fast - both are often caused by a sense of entitlement and overestimation of one's own abilities.

Earning your own roll is a crucial part of the poker experience - it can't be replaced by a study plan, $1000 and some books..