[TorontoCFE]

When you are talking about a six-figure poker income, you are definitely safer than sorry. If you have substantial other income, then putting that at risk is not worth it.

I have seen no evidence that earnings the 1st year are treated differently than later years. CRA doesn't care that it's your 1st time making big bucks. It may take them more than a year to catch on, but legally the liability is the same. The facts may be stronger the longer you've been at it, but they will still want their cut of every year.

As for being a professional gambler, I've always said "good, call me that". Then you can deduct a lot potential expenses EVEN WHEN YOU HAVE A LOSING YEAR. If you have a bad year, well then poker losses can be offset against your day job earnings. You can't do that if it's considered just a hobby. If I decide to turn pro and give up my day job, I'd love for CRA to think of me as a pro gambler.

I am in the Toronto area (west end).
While I normally do not do public tax work, I don't mind helping you out.
My day job is as a CFO for a smaller, high-tech company and I do investigative & forensic accounting projects on my own.
Poker is really my 3rd income, but at least I have the poker player's perspective in these matters.