I agree that it helps if you're half crazy to use the award engine. Imagine if you had to use it as your daily job?
I've also experienced the award calendar not syncing up with actual flight miles most click - however, in these instances, amazingly perhaps, the award calendar is accurate. Where I used to see a patchwork of yellows and greens, when the availability opens up, I see 25+ days of green to yellow.
I feel like Captain Kirk in front of the wormhole - who knows when it'll close?