To the OP, I remember being that guy as far as climbing on basic stuff because I couldn't afford anything more. It was always a stress inducing process to buy something new that was touted as a time saver. Money was exceedingly dear and it was tough as a single, sole support parent to justify the cost on a maybe. That's still a habit that hasn't died.
I did though, carefully acquire new tools and mechanical devices which did make life easier and more productive.
His reasoning is likely a combination of money, confidence, learning ability and comfort. Get to know him better and introduce stuff to him to try in a nonjudgemental way.