The right pump will not leave you red faced. The road morph will take a tire up to 100 PSI quickly and easily. I'm not a believer in CO2. I've known guys that went out with two cartridges and ended up phoning in the troops. A good pump will never fail you.
The preglued patches are like pissing into the wind. THe stars have to be perfectly aligned and you have to do a perfect job of application or they won't stick. Why bother? If you're going to patch a tube, there nothing as sure as a properly vulcanizd patch. After a tube has been patched a few times, I replace them.. You always hope you don't have to patch on the roadside, but you go prepared to do so. It's far better to swap tubes and do your patching at home with a beer. I usually let the punctured tubes pile up and patch several at one time.
Chain breakage is rare, but it does happen. I used to carry a chain tool and used it once for something that should have never happened to start with. The chain tool found its way out of my bag. I was the kind that could darned near overhaul a bike with all the tools I carried. I found I could ride much faster with only minimalistic (and realistic) tools.
You'll find your own comfort level with what you carry, though... Use what we say as a guideline and decide for yourself what you need and don't need.
Mark
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Bicycling is my drug of choice. Followed closely by beer.