zagraniczniak: You need to make a conscious decision how much to use the wind, or fight the wind, or whatever.
Tiger spoke to this in a way a few years ago. "Pick a putting line, and trust it."
Knowing when to hit ding, or miss ding is something that comes with a feel for the shot. For me, I ding all drives and iron shots (or at least I try for ding) using the aiming cursor. For putts, I use the aiming cursor for any putt longer then nine feet. Again, I've developed a feel for missing ding on the shorter putts. However, it certainly isn't an absolute.
Also keep in mind, the amount of off-ding break has to continually be increased as WGT ramps-up the programmed randomness. I remember back in December 2009 before the update, you only needed to miss ding by an 1/8 inch to easily sink a 8 foot putt with big break on Kiawah. Its now been moved-up to 40%+ of break at least on longer putts. A rule of thumb for me on a four foot putt is, 10 feet of power and 30%+ of break. More feet of power on uphill putts.
I wonder if the off-ding putters will eventually have to use 100% of break to sink a putt? LOL!