It’s both surprising, and not, if you think about it. The way I’ve usually seen it happen is first the rear tire goes flat, then the front one. My theory is that both tires went through the same pile of glass/thorns/metal bits and they both picked up junk. the reason for the flat occurring on the back first is because there’s more weight on that tire, so the offending article works its way through the tread more quickly.

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Be organized. “I like having everything be really small and super organized. I put all of my tools in CamelBak’s Tool Roll. It’s got little compartments, and I can separate tire changing stuff in one place, stuff like extra pedal cleats or an extra derailleur hanger in another, and it all rolls up into this tidy pouch. If I do have a repair, I can pull that one thing out and lay it out on the ground and it’s easy to work.”
On a very sunny Saturday I had a rear spoke break - you can imagine that no shop was willing to promise a quick repair! I was so fortunate to find this shop and will come back - Andy not only told me to come down and he'd get it fixed, he had his assistant work with another couple while he measured, cut to the right size, installed and trued the wheel while I waited! It was awesome, and the whole place had a great feel and good people. Best of all he charged a very fair $20 for all that work - I would have paid a premium for the quick service! After experiencing lots of attitude at other shops and poor service, this was a real find. I hope you will check them out, they have a great selection of bikes and accessories too! Good people and good craftsmanship should be rewarded.
Unlike floor pumps, most hand pumps do not have pressure gauges. To get readings during my original round of testing for this guide, I built a special rig involving simple hardware-store parts. But the experts I spoke to seem divided on the usefulness of gauges. Half thought they were unnecessary, added bulk, and drove up cost. Why do you need a gauge if you know 100 pumps inflates your tire? But the other half liked them, because the “thumb test” is notoriously inaccurate.

The Knights Helping Knights Pantry is a student driven program at the University of Central Florida with the goal of assisting students through financially tough times. Donations that are either brought to the Pantry or are left in one of our 15 drop boxes on campus are provided by faculty, staff and students. Student organizations, departments and individuals on campus also organize food drives that benefit the Pantry.

First, I researched. I looked at Amazon’s top-rated products and their user reviews. Then I consulted Bicycling magazine, Gear Junkie, Bike Radar, Outside, and the occasional bit by Lennard Zinn via Velonews. I also found some worthwhile discussions at Bike Forums. Then I spoke with four experts, Ramona Marks, Scott Karoly, Cari Z, and Alison Tetrick, riders from all across the spectrum, who tour, repair, and race.
As you mentioned, it is surprising how often you can get multiple flat tires on while riding, particularly on longer sprints. The tip about bringing a patch kit in your bike repair kit can be incredibly helpful if you’ve already had one flat tire. I agree that all you listed seems like an awful lot to carry, but it’s always better to be safe than sorry, isn’t it?
^{This is the shop I hoped to find when I began commuting two years ago. I'm a daily commuter and I love knowing that these guys will help me almost anytime that I need it. Andy, Jake and Brad listen and make sure to help me as best they can and are always speedy about it. Additionally, they encourage me to do my own work on my bikes when I have the time/when they know I'm capable and I really appreciate that encouragement.}
Don’t rely on others. “People need to recognize that now there are different cassette sizes, so there are different chains depending on what gear you have. A lot of people are like, ‘Oh my friend is always prepared they always have the stuff, I’m not going to bring anything.’ All of the stuff now is very bike-specific, and you have to have your own package of stuff.”
A pair of disposable latex gloves:  Not absolutely necessary, but good for keeping grease and grime off your hands during a repair.  Also, nice to have in an emergency when it starts raining and the temperature drops 20 degrees and you don’t have a pair of regular gloves.   Just keeping your hands dry and the wind from directly blowing on them makes a huge difference in comfort.

Whether you ride a single, 7, or 10 speed bike or anything in between, you will need a slightly different chain. The major difference is that they come in varying widths to accomodate the different spaces between the gears, but quality of construction is also a factor in choosing a chain. Inspecing the chain should be a part of your regular cycle maintenance procedure- It’s important to keep a chain well lubricated, but oil will also attract dirt and so different oils for specific riding conditions are available. Remember to clean your chain regularly to get the longest life out of it and the gears.