Change and a $20 bill: In case your cell phone’s battery dies, it’s nice to still be able to use a payphone if you need to. Also, the $20 is a great thing to have in case you lose your wallet or have some other mishap. I’d rather be able to sit in a coffee shop or fast food restaurant when it starts raining while I’m waiting for my friend or cab ride, and a hot cup of tea or coffee or the beverage of your choice and a snack makes it all the more pleasant. Just try to remember, this is for emergencies, and if you use it, replace it ASAP!
If you own a bike, you need a flat-fixing kit. It’s really that simple. Sure, maybe you’ll get lucky and get a flat close to a shop, or the buses will be running on time for once, but even with all that going for you, getting stranded across town will cost you time, money, and precious sanity. You can put together a great kit in less time than it takes to read this guide.
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?
Basically, you’re stuck with toggling between systems for the advantage of a few pumps, and it doesn’t seem worth it. In the original iteration of this guide, I tested 12 pumps and inflated three different tires completely full to their psi rating, and measured how many pumps it took. Yasuda did similarly for his revamped full-length exploration. That’s 36 tires, and I can guarantee there is no difference between 50 pumps and 100—it’s all terrible.
The thumb test is the fine art of pressing on the tube with your thumb to see if it’s inflated. During testing, I took a pressure reading out of curiosity, and to the touch, road tires feel fully inflated around 30 psi. How pathetically sad—30 psi!—when you’re probably trying to reach at least 60 psi on a mountain bike, 70 or more on a hybrid, and it only goes up from there.
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.
These guys are awesome. After work, I got to my bike to discover my back tire was completely flat. It had a slow leak, so I was able to pump it up enough to make it to their shop. I got there 10 minutes before closing and they were able to fit me in. They replaced my tube and picked all of the glass shards out of my tire. Awesome customer service and they saved me from having to do this myself in the dark and the cold.
If you’re going to use the chain whip you just made, you’ll also need a way to get that cassette off. A lockring remover is a must-have; unless you use one of the shady removal methods I’ve seen on the internet—which I wouldn’t necessarily recommend unless you don’t care much about the condition of the wheel after you use them. I recommend Park Tool’s iterations here that cost about $6, but you’ll need to buy the specific one for your brand/type of cassette. (By the way, I’m assuming you already have an adjustable wrench laying around somewhere to use with this tool. If you don’t, well, you’ll need one of those too.)