Gambling is a risky game

For those of you that fly often like me (5+ times a year), we try our hardest to find flights that a) leave and arrive at a decent time, b) that aren't incredibly booked to the point that you're about to get the last seat and c) is at a reasonable price. Now, since I've moved out to Victoria, I've been flying to Calgary and to Toronto often and I have a good grasp of what a decent price is for a seat.

But here's the problem:

It's 2 months before your desired flying date (in this case, August 18th to Toronto from Calgary.) You know that you can get a seat sale for around $149 or $139 to Toronto, but at the same time it's summer, so the demand is high. And then, you stumble across a seat sale on WestJet for $189 one way. You're thinking "hey, that's not bad!" But, remember, you still add taxes onto that. So you then see that the total price is $245. Well, it's not that bad, but what if.... what if you're able to find that same flight at a cheaper price down the road? Or, what if this is the only seat sale that will bring the price that low? Should you buy? Should you wait? What the hell to do?

You see, buying an airplane seat at a cheap price is like gambling - you can sit out and realize that that was your opportunity to play, or you play but then find out that it would have been better to sit out! For this precise reason, I *hate* buying flights. The cost doesn't bother me; what bothers me is finding out a week later that the same flight that you're on is cheaper by, like, $50!

This is my dilemma right now - WestJet has a seat sale for $189 to Toronto from Calgary, but I'm not sure if I should buy. Granted, I have a $99 credit from them which makes the prices cheaper, buuuuut what if another seat sale comes along and the price is lower than $189? But what if it isn't?!

You see, this is frustrating!
Lady S.