Just booked my Southwest flights from Chicago to MCO for June. Came out to be $389 per person round trip which is about $90 more per person than I've ever paid before. I've read that the best time to book a flight cost-wise is like 6 or 7 weeks before, but I have no patience for that
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I hate to throw money down the drain by not waiting a little longer but I also want to make sure I get a flight on the day I need to come home. Who knows maybe you wait too long and prices don't drop
I agree with your approach. While this method may not get you the absolute rock bottom price, your peace of mind and meeting your time needs is worth something, too. Besides, prices on everything else go up and I don't mind paying a little more each year.
Right now I'm waiting for some better fares from here in western Canada to MCO in mid November. We have absolutely no flexibility regarding which days to go and lately, every day around ours in both directions is way cheaper than the days we have to have. Frustrating.
So I saw a "if h*ll freezes over..." price that I would grudgingly pay (and were the exact flights we wanted), if I had to and put a "Farelock" on it just to have this as a fallback position. Today, I saw a better price for our days but with a very long layover on the way back.
So, at the end of the farelock week, I'll have to decide whether to buy at that fare, get the less desirable layover and save a few bucks, or if we're really lucky, our perfect flights will drop even lower that the poorer fights. Or, of course, keep looking, in the hopes that "something" will come along.
By the way, most people will tell you to buy at a price you find acceptable and stop looking. Good advice but I never take it. Even when I've bought at a higher price than I've wanted, the flights we need have never come down in price and we buy as soon as we can in most cases. True, you might get a better fare a few weeks out but on a route to a warm place during the winter, those flights always fill up and it's just a matter of when they do. It's even harder over Christmas or March Break season.
Yeah, it's great to get great deals on airfare, but sometimes you just have to bite the bullet and pay a bit more to get the flights that you really need or want.
Sorry for the long-ish post!
Southwest is not yet open for our dates (and I know we have plenty of time to book) and I'm hoping there is better news there. I would prefer SWA anyway. I know that for our July trip USAirways was not very competitive (I guess not so surprising since the merger). Thank heavens for SWA. 
