[rubzah]

For the health benefits, without some of the downsides, I believe it is preferable to drink coffee when you are not tired. This way you don't get a crash later, because there is no adenosine build-up (the 'tiredness' signaling molecule that caffeine blocks). I believe this also helps to prevent addiction, because there is also no up-regulation of adenosine receptors.

This works great if you drink coffee for the taste, rather than as a way to stay awake (which works in a pinch but is counter-productive over the long term).

[mekdoonggi]

I generally always sleep well, but enjoy a nice big cup of coffee in the morning. If I'm really sleep deprived, I switch to black tea. Seems odd because you'd think less caffeine would be worse, but the tea is easier on the stomach and somehow "evens out" the sleep deprivation better.