Yeah, you won't find a good volume of people on the forum specifically familiar with the Calgary market, so it would be general concepts:
1. Except as a true home (i.e., unconcerned with costs/loss/profit), buying is speculating. Selling as a financial strategy is too.
2. On the forum, we're clear that we have zero idea what any given market will do -a single stock, a single currency, a single real estate area or type. We acknowledge that any market can go up and down, and probably will, and that we rarely know when it's going to do what.
I'm usually biased toward selling, just because homes cost a lot to maintain -taxes, strata fees, maintenance, insurance- and those costs can go up significantly at any point, and an area's tenancy laws can put a landlord at too high a risk. I prefer index funds. But, some people on the forum love holding real estate. It's their only option for investing OR they scored great deals, love dealing with people, etc.
No one can know what condos in Calgary will or won't do. You're already interested in going that route, you can sell for a profit, you know how to invest the net well, and those three pieces are all you can know for sure. Buying or selling always brings the risk of losing out, but so does not buying, not investing, and not selling.