Book something you're happy with and always check back to see if you can improve on it.
That's my best piece of advice for truly getting the most value out of travel,particularly when you're redeeming miles & points. It goes beyond miles & points, though, and is true of "revenue" travel as well,particularly for hotel stays.
More than ever before it's important to be flexible when redeeming miles. Airlines are holding back increasingly award space, so ideally you lock in something you're happy with when you're ready to draw, and then just sustain checking back. Over and over and over again. Let me give a few examples of "successes" I've had with this method recently.
I'm going somewhere to original Year's which is typically nearly impossible to find award space to. I only booked a few months out,and was shocked space was available. The "catch" is that the moment flight was in economy. Ultimately it wasn't a huge deal, given that it was an A330, and meaning we could snag two window & aisle seats together.
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Source: boardingarea.com