I think I would teach him in my shop on my tools until he was ready to set up his own bench. Then I would loan him the press of his choice, Chucker or Lee. No need to press your own preferences/prejudices on him as opinions of reloading equipment fit the person that owns the opinion. When he's ready he will probably return the press after he has purchased his own. I never minded using other's tools, but got a lot of pleasure and experience/learning from researching and buying my own...