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.)
Next to everything else that might go wrong with a bicycle on an extended ride, a flat is a relatively minor issue that can be easily repaired trailside, if the right tools are at hand. If they aren’t, a quick fix can turn into a long walk. Well-prepared riders will perform a tune-up regularly and clean their bikes after every ride. For the less-diligent, a well-stocked repair kit will suffice.

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Yes, bicycle shops generally provide repair services. A typical list of offered services includes regular service/adjustment (including safety check; and  brake, drivetrain, and tire inspection); premium, and annual service, which is a more extensive tune-up. More specific repairs include drivetrain tune-up, brake system tune-up, flat tire fixes, brake repairs, cleaning and touching up the bike frame.
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.
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.