I thought the exchange downtown had some reps there to help you with the wallets etc? Kind of like bank clerks.
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.