I used the Continental gatorskins on my Southern Tier Ride last year, and yes they were hard to get on the first time. I had NO flats in 6000 miles, 3200 on the long ride and 2800 other miles. I did have to change the tubes twice due to a defective pump that pulled the valve out. It WAS difficult to get the tires back on, and YES I did use tire levers, very carefully.

I just put a brand new pair of gatorskins on for my next long (2000) miler coming up in ten days. I know that they will be tough to change but the puncture resistance of these tires is worth every bit of difficulty on the one or two flats you might get. I keep mine inflated to 105# or even more and have not had a problem. They do loosen up a bit.