In a 'normal' market, selling first is conservative, but in the perpetually hot market of central Toronto, selling first means you may get stuck without anything to move into because it's so competitive out there for buyers (especially for the best properties- I'm assuming you don't want to buy a piece of junk!)
Your agent should be able to give you a very good idea of exactly what your condo will sell for, within about a $10K variance. I doubt this will make or break any subsequent purchase. Of course no one can predict the future but generally a unit in a building with high turnover should be fairly easy to predict the selling price and time it takes to sell (given the property is showing in top condition).
Bridge financing is not as bad as it sounds. almost everyone does it when buying and selling. the fees are not as bad as you might think. the banks can set this up with very minimal effort.
also, quick closes are becoming very common these days (that is, finding a buyer for your property who can close in around 30 days or less), so if you buy first you will likely be able to sell quickly and close quickly on the other end assuming you play all your cards correctly.
if you do decide to sell first, make sure you get as long as closing as possible to ensure yourself as much time as possible to find your next property.