You're absolutely right about the real estate market in Toronto.Welcome to Toronto! Was fun reading through your "advice/diary entries". Always fun to read about people choosing to settle in Toronto. Just wanted to comment on your plans for real estate investments. The Toronto housing market has been very lucrative as an investment but I would imagine that your colleague started investing over 5 years ago and perhaps at the pre-construction phase. I have a hard time believing that if your purchased today the returns would be that good unless you create a rooming house. Just wanted to temper your expectations. Also given all your hard work and your savings I would treat yourself to a $20 meal a bit more often Trust me you never know what can happen!
He buys houses (duplex/triplex) outside Toronto. To quote him, "only idiots would buy houses in Toronto now."
We also exchanged our schemes on tax minimization in Canada, the US, and the Netherlands, using various corporate structures. The more I talked to him (and two other Jewish colleagues), the more I felt that I should have been born a Jew myself