Gatorskins aren't my favorite tire, though if you want a reasonably fast, durable, long wearing tire for a decent price, they are very hard to beat. In the past 3 years, I've ridden probably close to 15,000 miles on Gatorskins with no flats that I can remember, except one instance where I hit a large angular rock descending a hill at 30+ mph. The sidewall was partially damaged but I was able to get 1000+ more miles out of that tire. The sidewalls are usually the first thing to fail with these tires only because these tires will wear forever, not because the sidewalls are more fragile. I usually get close to 3000 miles per tire, starting with the tire in the front and eventually rotating it to the rear. If you want to avoid premature sidewall tears such as the one posted above, inflate your tires properly and avoid debris. Occasional premature tire death will inevitably happen, regardless of the quality of your tires. Buying an expensive tire is a gamble. A nasty rock or pothole taken at speed can destroy it just as easily as a cheap tire. However, premature sidewall damage from potholes and debris is much less likely with larger tires, regardless of sidewall construction.

I've never tried randos, so I can't really make a comparison.