In addition to the Rema patches, put a new tire tube in your kit. The best method for dealing with a flat roadside is to swap out the tube and save the task of patching for later. If you’re not sure what size your tires are, it’s printed on the sidewall of the tire. This inner-tube buying guide has some photos of where to look. What brand is almost irrelevant as many tubes get manufactured in the same place, so whatever your local shop has behind the counter for under $10 will work fine. The only reason to spend more would be to save weight.
That’s a reality of all hand pumps—it’s really hard to get a tire up to pressure with these things. So another reason Lezyne pumps are so good is because you can actually keep pumping longer than any other brand we tested. With excruciating effort, we could get the Sport Drive HP to pump tires to 90 or 100 psi. It still wasn’t easy, but it wasn’t impossible the way it was with some other models.
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?
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.
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.