A wrench that fits the hub nuts: If your bike has quick release front and rear wheels, you don’t need this, but if you have an internal hub on the back, such as the NuVinci, a wrench that fits is a great idea. 99% of the time, this is a 15mm wrench, but you should check your bike. A 6 inch adjustable wrench can also work, but it will be heavier, and when using an adjustable wrench, you do need to take more care to not round over the nuts. A fixed wrench is the best choice. Some multi-tools have a 15 mm wrench built in, but again, if you have limited hand strength, something with more leverage is a great idea.
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.
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.
Brakes come in a variety of designs depending on the age and style of your bike. Rim brakes offer more modulation but have less stopping power, so are more suited to riding on the roads. Disc brakes can provide huge amounts of stopping power so are best suited to off road riding, although ‘V’ rim brakes are also well suited to mountain biking. All brakes use a friction system to stop the movement of the wheel, so regular checks of the contact pads should form part of your regular cycle maintenance.