A multitool is a highly versatile piece of repair equipment that can address most of your maintenance needs. Ideally, you should use it before a ride to tighten and adjust everything properly, but sometimes it’s necessary on a ride as well. If you encounter a loose screw, realize your saddle height is not right, or that your brakes need tightening, you will be happy to have it.
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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?
Mini Pump:   This actually goes on the frame of your bike, as it’s a bit too big for most under-seat bags.   Coming soon, we’ll have a review from Bill of his very favorite one, but a good pump is a lifesaver.    Some people instead carry a CO2 inflator, which is faster and easier to use but does require disposable cartridges, and each time you have a flat, you’ll need at least 2 of those cartridges.  There are combined pump/inflator tools that we’ll also talk about soon.
Modern bottom brackets use a sealed bearing type construction that keeps water and debris locked out, so they seldom go wrong. Maintenance is impossible so they need replacing when they do wear out. Older style cup bottom brackets need to be re-greased every now and again, and occasionally will need to have their bearings replaced. There are a lot more teeth on the chainring cogs than those on the rear cassette, so need changing less regularly. Cranks usually a solid one piece construction so there is not much to go wrong.
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