From personal experience I had no problem learning Mac-OS, which I stumbled around in at first but didn't experience any major problems until much further down the road (when I was capable of dealing with them).

On the other hand I downloaded Ubuntu last month, and after taking several hours just to get onboard wifi working (xps m1330), I lost all desire to use it further.

For me, gradual hurdles vs. massive roadblock after roadblock is the difference between enjoying the learning process instead of dreading it.