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.
Spare tube:  Sometimes, a tube is just too damaged to be patched, or has had a failure such as the valve stem breaking off which isn’t something that can be patched.   To save weight and space, I usually keep a lightweight version of the right size tube for my bike.   Since one of the first things I do with most bikes that I own is switch them over to heavy-duty thorn resistant tubes, I just take one of the originals and put that in the toolkit.
2) On my second day, the pannier bag fell off and got lost after I stopped for lunch, which required locking up the bike somewhere, so I took the bag into restaurant and re-attached it using the two velcro straps on the rear rack. I've used many panniers before, thought I did it correctly. But apparently I did not. So I paid $55 (cost) to replace everything in bag and bag. In hindsight, I wished I'd put a bungee around bag straps to really secure it to bike. PROBABLY MY FAULT.
Now you might be wondering: “I’m carrying a tube; why carry patches at all?” As insurance for the unforeseeable. Wirecutter senior editor Christine Ryan admits she didn’t use to pack them, but said, “I’ve regretted that decision when I’ve had a flat on a ride, used my spare tube, and then, half an hour later, had a second flat. Also, lots of people aren’t very good at figuring out—or don’t take the time to figure out—what caused their flat and remove the cause: thorn, eensy bit of glass, whatever. Then they promptly have a second flat, and everyone else laughs at them.”
Maintenance is the best prevention. “Prevention is the best medicine, and if you’re taking care of your equipment it’s super key. Bikes don’t just fail. If they’re in really good working condition and you clean them at night, and you’re religious about it, bikes are kind of like cars — they’ll start talking to you if something is getting worn or getting creaky or needs to be replaced.”

Over the years, I’ve come across plenty of articles that claim to tell you how to build up your cycling toolkit for cheap. Somehow the word “cheap” stops recurring in the long list of “essential” bike repair bits and pieces. The truth is, there is no real way to build a whole shop of tools all at once without plopping down a few hundred bucks. But in an attempt to show everyone that not all of us truly need a full complement of bike tools, I present the truest, most budget-conscious, and barest of bones options to you.
One key difference, that you can see in the photo, is that the BV uses buckles instead of Velcro on the straps that attach the bag to the underside of the saddle, something much more important than it may seem. A pair of bike shorts (or any shorts) will shred quickly if they’re rubbing against that tiny bit of Velcro protruding from the side of the bag, and it’s sure to destroy expensive sweaters and gym clothes if you stuff the bag into your backpack or messenger bag.
All multi-tools are not created equal, but most with a plethora of features will get plenty of the jobs done. I personally like, and use often, the Lezyne RAP-21 LED tool, which will run you around $30. I like it because not only is it a high quality construction, but it has just about everything you’ll need, plus a sweet mini light. This will give you a chain breaker, spoke wrench, disc brake wedge, and all the most often used Allen keys and drivers. We’re talking a decent number of tools for 1/4 of what they would cost buying them separately.
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?
Friction gear systems are a lot simpler to adjust, because the movement of the derailer cable can be modulated as you ride, every time you change the gear- they require less cycle maintenance. Modern index shifting systems are a little more complicated because each ‘click’ must release the exact right amount of cable to allow the derailer to move the correct distance to move the chain from one gear to another. Setting up and adjusting a derailer is not difficult and requires only basic tools, but there is a methodical procedure to follow.
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