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?
The Pedro’s lever slipped only once throughout testing, though that may have been my fault because I was spaced out after changing 16 different tires. So they’re not foolproof, but they are far and away more reliable than the next closest competitor, from Park Tool, because the small, rounded tip on that one is hard to keep seated under the tire. Not impossible, but I wouldn’t choose it over Pedro’s.
Basic first aid supplies: A few bandages of varying sizes. 6 Aspirin, or other OTC painkiller of choice. A few alcohol pads in sealed foil packs, useful for cleaning grease off grease and grit off of the bike, and also cleaning cuts on yourself if you take a spill. 1 day supply of any prescription drugs you need to take regularly. Wrap these up in tinfoil and tuck away. It might just save your day.
Next, two-stage designs. There are two types of hand pump. HV (high-volume) pumps, ones that pump a lot of air but don’t have a lot of pressure, which are used for mountain bikes. The Lezyne Alloy Drive is a high-volume pump. Then there are HP (high-pressure) pumps, which pump a small amount of air but can inflate to very high pressures and are used on road bikes. Our top pick is a high-pressure pump.
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.
Keychain style flashlight or headlamp, LED type, not incandescent: The keychain style is tiny and lightweight, the headlamp style is a bit bulkier but easier to use. You can get these for a couple of bucks or less at the local big box hardware store. The LED ones are lighter, more durable and last considerably longer. Very useful if you need to make a repair after dark! I keep a keychain style one as a backup as I normally have a headlamp in my backpack.
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.
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.