There's Bitcoiniacs at Waves, and the Bitcoin Co-op guys in Gastown. I suppose those are options too.
But this individual is mostly interested in price speculation as part of a diversified investment portfolio. I'm not sure it's important for him to learn about bitcoin wallet security at this point in time. Perhaps that can wait.
that doesn't sound too wise. Bitcoin is meant to encourage personal responsibility. plus it will make him learn and appreciate what Bitcoin is all about.
speculation on the price is somewhat dependent on one being able to hold onto one's coins w/o getting scammed.