A two-stage hand pump tries to marry the best features of both types of pumps: the quick inflation of high volume that can achieve the higher psi ranges of high pressure. But to steal a quote from our floor pump guide, “You pump eight times or you pump 10 times—what does it matter?” That’s a quote from Daimeon Shanks, who at the time was a mechanic for the Garmin-Sharp pro tour team—that’s right, Tour de France, baby.
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?
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.