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?
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.
Friction gear systems are a lot simpler to adjust, because the movement of the derailer cable can be modulated as you ride, every time you change the gear- they require less cycle maintenance. Modern index shifting systems are a little more complicated because each ‘click’ must release the exact right amount of cable to allow the derailer to move the correct distance to move the chain from one gear to another. Setting up and adjusting a derailer is not difficult and requires only basic tools, but there is a methodical procedure to follow.