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.
It has some useful information for basic repairs... not so heavy on the maintenance side but there is some in there. The pictures and drawings are in black and white, but mostly visible. Only a few are difficult to see. However, they are in 2-dimensions and they don't show you HOW to do the thing, they only show you the general area and the part you want to manipulate. The phrasing in the instructions can be hard to follow without a good visual reference unless you're already a master bike mechanic (which you aren't if you're thinking about buying this). So, buy this for general reference and rely on Youtube for video. The two together are better than either one alone.
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?
Any bike that gets ridden seriously as transportation or on long rides needs at least a basic tool/emergency kit, and the knowledge to use it, unless the rider is always in a position to call a friend with a car or a cab when their bike needs a quick fix on the road. If you never travel more than a few miles, this can be overkill, and calling a friend or a cab may be just the ticket, but if you want to be more self reliant, this is something you should seriously consider. This list may sound like an awful lot of stuff to carry, but really, it only weighs a few lbs and fits in a small, under-seat bag that comes off quickly so I don’t have to leave it with the bike if theft is a concern. If you always carry a regular rack top bag, you can also just put all this in a small nylon bag and throw it in there, but I prefer an under-seat bag.
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.
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.
The fabric attachment system is low-tech, but that seems to be helpful, as it can adapt to seat rails of different widths. One fancier option you might see on more expensive seat bags is a quick-release mount that you install under your saddle. But those have a fixed width, and therefore can fit under seats with only those exact specs. Brooks saddles, for example, are too wide for these mounts.
There are two major types of headset- older, threaded headsets that have a quill that drops into the stem of the fork creating an interference connection, and newer threadless headsets that the stem is bolted and clamped on to. Flat handle bars are preferred by off road cyclists who can ride in a more upright postion whilst still having the controls at their fingertips, whereas drop handlebars offer more cycling positions and are favoured by road cyclists who typically spend more time in the saddle. The controls attached to the different styles of bar are operated and maintained in different ways.