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Volhq does have the ability to track these. I had him add it in around 3 years ago. Just go into Advanced Options and choose "Before" under "Short leg expiry before or after earnings".

@FrankTheTank I'll keep working with the "pre-pre" trades and if I decide to trade any, they will most likely be a single. I'm willing to take the SO approach as a successful given, since it has been so for me. But, like you, I am always looking for another angle. And trying new ideas is fun if you don't get stupid. My wife has a t-shirt with a picture of John Wayne in his Marine getup, the quote is "Life is tough, tougher if you're stupid", I try to live by that sentiment, often successfully.😁

I'm not so sure about it. In order to risk the same amount, you need to reduce the position sizing by half. Is the average return double? I highly doubt it.

As an update - I spoke with my accountant. In my particular situation she advised to report profits as capital gain. It was primary based on the fact that I have a full time job and profits from trading were very small comparing to my overall income. However, if I become very successful (which I truly hope will happen one day) or switch trading full time I should call back to reassess the situation. As a general comment, she noted that there is no strict CRA guidelines (as we have discussed above) and all "regular" guys doing trading on a side fall in a grey area. This means that either way I decide to report my gains or losses I should be prepared if CRA comes and re-assesses them differently. And on a very special note, she was very surprised that I didn't blow up my account in my first year and even have profits to report. For that I would like to send kudos to @Kim and @Yowster for creating such a wonderful community for us.