Sunday was my first long ride of the year in this part of the world, and my all-time worst record on fixing a flat, and I blasted through four new tubes, two CO2 cartridges and a pump before finally getting back on the road. It was a combination of bad patch job (my patched spare tube), dud inner tube (biking buddy's spare), incompetence with CO2 cartridge (my fault again) and general ineptitude at getting very tight tire back on a fairly deep rim without pinch flatting (both my fault, and the fault of the super nice racer dudes who offered up their own spare tubes and then stopped to help). I even managed to mess up my pump when the valve stem broke off inside it and refused to be dislodged, so had to borrow a pump as well, to complete the catalog of errors. I ended up repatching the dud patch job, and then replacing the tube for the 4th time and (for the first time) sliding the tire back on the rim as though I had been doing it all my life. But I have little confidence in my ability to do the same next time.

I have Continental Grand Prix 700/23 tires, and Fulcrum Racing 7 rims. Rim tape was new at the end of last season, after a series of flats, but the tires probably have several thousand miles on them. I'm thinking of switching to Gatorskins to reduce the propensity of the tires to flat.

So my questions:

Is there a tire that won't break my wrists or bend my tire irons when I try to force it back on a relatively deep rim?

Does anyone have any favorite tire irons that actually work?

Will Gatorskins help, or will it just be even harder to get the tires back on?

And why is it always the rear tire that flats?

Welcome any and all insight.