A watt is the measurement of the amount of energy used to accomplish work (this can be physical work, electric work, etc.). To put it in perspective a typical incandescent light bulb uses about 60 watts of electricity per second and an average PC power supply can provide 500 watts per second at peak load if that's what it is rated at. Rarely does a power supply reach peak load unless you have one that provides too little electricity to your system. If a power supply does reach peak load and operates at that limit for an extended period of time it can cause damage.
The 50% aging setting is pretty high I wouldn't worry about that too much. As for peak load very rarely does a PC draw as much electricity as it possibly could. Having your processor and video card running at 100%, plus all your hard drives/CD-ROM drives accessing to full potential, and all your add in cards/components being utilized to 100% of their capability just doesn't happen very often even when gaming. For example when was the last time you were playing a demanding game at the highest possible settings while copying large files from across your network, while burning a DVD, playing music, and copying large amounts of data from one hard drive to another?
There is also another factor the PSU calculator doesn't take into consideration and that's amperage. Amperage is the measure of current intensity and a lot of power supplies that claim high wattage at a low price lack the amperage to properly power newer components (higher end video cards for example).
As for the power supplies online having high death rates that's to be expected. A lot of them are of low quality. There is really only a handful of high quality PSU manufacturers and even their products vary in quality, but even their best products aren't going to have a 0% fail rate.
Should you spend the money for extra headroom? I can't tell you that without knowing what's in your system right now, what kind of power supply you have right now, and what kind of power supply your friend is giving you.